That particular reaction is Pd(II) catalyzed, not Pd(0) - JACS 1985, 107, 1781 ("A Pd(0) species such as (Ph3P)4Pd does not catalyze reaction after 12h at reflux in THF") Related references on mechanism: JACS 1994, 116, 4255 | Acc. Chem. Res 1990, 23, 34 There are however probably similar, Pd(0)-catalyzed reactions with different conditions/ substrates (had a quick look, e.g. JOC 2004, 69, 6697)
@Jm Cresencio that would then mean that Pd(0) is catalysing the reaction, which is the purpose of the use of Pd(OAc)2. the acetate ligands are supposed to be quite labile so they come off quite easily, allowing catalytic pathways to initiate requiring the non-complexed Pd(0). a Heck reaction is one such example of this catalytic pathway being used in synthetic application.
I clicked this knowing I wouldn’t understand a thing.. I indeed didn’t understand a single thing, but it was fun to see all those hexagons saying “Me.”
Hi, perhaps you will like my channel with review of some new chemical publications. I try to keep the videos as simple as possible. th-cam.com/users/ChemNews
Welcome to the TH-cam graduate student seminar! I'm a biochemist with a decent organic background, and this teaches me so much. That gold-catalyzed cyclization with a cyclopropane & alkyne made my jaw drop.
I AM SO HAPPY I FOUND THIS ACCOUNT. As a chemist in the drug Feild I am blow away at this synthesis. I complain at a 6 step synthesis...kudos to these nerds
Hi, perhaps you will like my channel with review of some new chemical publications. I try to keep the videos as simple as possible. th-cam.com/users/ChemNews
Great video, I am waiting for more!! Take your time of course, is not easy to summarize a total synthesis and the target audience is very limited, but I am sure that if u keep publishing this kind of videos, all the community of synthetic organic chemist will know about you!
I cannot understand antything but somehow it seems super interesting. Like puzzels for really intelligent people. I loved chemistry back in middle school. Shame that I lost it in the high school. It still fascinates me and I wish I could understand it.
Thank you for your videos, they are very interesting for an undergrad like me interested in total synthesis and retrosynthesis. Keep up with the good work. From Italy.
Being a synthetic chemist researcher it is quite interesting and inspiring to continue work I know that it is not easy as it seems on paper......it takes years to design such a complex synthesis
I wanna thank the TH-cam algorithm for suggesting this to me. This is the first video I saw and its the one that made me a subscriber. as a second year chemistry student myself, I am proud to say that I understood most of what was going on.
Please keep making videos if you can, I know TH-cam and life in general don't reward content like this much but what you do is important to get the small group of interested people to dive into this subject and potentially go on to make important discoveries.
Hello, GREAT material with a perfectly paced delivery. Please make more videos, these are so informative and make the material much more understandable/accessible. Thank you for your patient and thoughtful insights to the chemical world!
I'm a Bio major but I have absolutely fallen in love with Organic Chemistry; so much that I'm now a Supplemental Instructor for Orgo 2. It's just so cool!
I've found ur channel on /sci/ months ago, had it bookmarked since then now that i got this vid recced i v become really intrigued to learn chemistry, i underwent chemotherapy and used taxol so this definitely relates to me, really appreciate the video hope to see more of
commenting for algorithm reasons!! these videos are awesome, and im in awe at your ability to digest big papers down into an engaging format! keep it up!
Recently i studied for special methodologies in organic chemistry and i was pretty amazed when you spoke about the taxol and the background, then you procedeed to explain the synthesis...
Many interesting possibilities in terms of reactions and approaches... and even more ways to "fail", leading to quite unique routes being explored Thanks for watching!
Great video, thanks for putting it together. Was nice to be able to recognise a lot of the transformations from my organic lectures! Modern day wizards, these guys.
So helpful. This has almost every reaction from my Total Organic Synthesis class. It's like a condensed version of the Modern Organic Synthesis book by Somfai. Thank you so Much. Really interesting synthesis.
Superb Total synthesis video. I was very excited by seeing this video. Total synthesis is good approach for applying, practicing organic reactions and retrosynthesis. Please upload more videos.
Great video! I'm glad I found your channel, I'm sure I will learn a lot. It's hard to memorise everything from such a blast of information but if you memorise one thing for each video, you will slowly be a better chemist.
These videos are great. I wish there would me more of them! I appreaciate doing neat and nice ChemDraws such as the ones you show take time, but it is worth the effort! I would certainly spread the news of this videos to other chemists I know would enjoy!
Currently working on my seminar presentation on the Baran lab's Taxol total synthesis route published mid 2020. It was cool watching this vid and being familiar with all of this stuff.
Through out the synthesis, bestbpart is, before disconnection, hypothetical functional group introduction -OH group like acid group on cubane and removal at end. Here did in two steps, thieves formation then treated with tin reagent. Might be can use novel methods, like triethylsilyl hydride to get product in one step to remove -OH group. Overall good lecture and I requesting you provide more and more vedios like this. Thank you.
Nice presentation! But I couldnt help but notice some mistakes. At 13:17 methyl triphenylphosphonium bromide is displayed wrong and at 14:45 there is a pentavalent carbon shown in an explanation of the NOE spectrum.
I'd really appreciate if you discussed how advances in machine learning are contributing to advances in chemistry with specific regard to reaction prediction, synthesis analysis, pathway design etc
Nice video and what a beautiful synthetic approach! I have only a point of criticism: you're too fast, at least for me. I would have liked more time to look at the structures before you removed them. I know that there is a pause button, but often I had to rewind a few seconds before pausing because you have already removed them.
One of my cohorts in my Graduate Organic synthesis class had to give a presentation on this molecule. He didn’t look like he enjoyed making the presentation though
At 13:17. Is it possible that the reagent used in the Wittig-reaction should be Ph3P(+)-CH3? Otherwise, where does the Br go? In the conditions given in the publicaiton there is Ph3PCH3Br written, probably with a missing comma between the reagents Ph3P and CH3Br.
Great videos! I have one request, though, to make things a bit more easy to follow. Could you use a 'laser pointer' of sorts, to guide us through the molecules as you discuss them? It's sometimes kind of difficult to know which part of the molecule you're talking about, and to follow what you're saying at the same time. Especially with these complex syntheses.
How did the team manage to protect only the one of the two OH groups in the step with PivCl? Is this reaction selective or more favourable kinetic product at lower temperatures?
I LOVE your videos!!! Thank you for the content. Have you considered a different mic or audio balancing software? I’m getting a very low volume when I wtatch
I really enjoyed the retrosynthetic analysis in this video, you do a nice job addressing the issues of complexity vs accessibility in a sparsely functionalized target.
Hey, I like your approach towards each video. here's a small detail that I would like to add according to my opinion. It would be more engaging if you add some background music. thank you very much. keep up the good work. (y)
I dropped out of school a single class before my graduation. I went for chemistry but I lost interest, i didn't understand the material or how anybody could learn so many arbitrary things and pretend that they deserve to pass the class. I had passed all of my classes with at least a 3.8, and I would have probably passed this but i just hated it. I like chemistry, but school is terrible. I did not struggle with analytical chemistry, only organic. Felt like everything was completely arbitrary and based off of how well I can memorize 100 things in a single week. Not my strong suit.
Really excellent channel. I'm quite new here, but I look forward to delving more into the channel. I'm curious, where do you get information on things like the total sale of drugs like Taxol? I see this sort of information in papers occasionally, as a way to motivate interest in a particular compound, but I never really know where to begin looking for financial information on pharmaceutical agents that I myself am making. I hope you see this, thanks!
What is the reason for the epimerization after treatment with the Ohira-Bestmann reagent? AFAIK, the Ohira-Bestmann reagent usually does not cause alpha epimerization, and I can't find an explanation in the paper. Edit: I think it is due to base catalyzed alpha epimerization of the aldehyde via keto-enol tautomerism. The potassium carbonate base used with the Ohira-Bestmann reagent is able to induce keto-enol tautomerism on the aldehyde, which leads to conversion to the less sterically strained epimer.
4:45 It's actually not the same depicted molecule. As you rightfully said it's a diastereoisomere... 😉 Greetings from another chemist. 😉 GREAT video though!
![[[OFFICIAL MV]] เอิ้นขวัญให้อ้าย- อ๊ะอาย สกุณาพร | ค่ายเพลงเป็นหนึ่ง](http://i.ytimg.com/vi/83x6L3X3qh0/mqdefault.jpg)
9:11 is there a reason to suppose, that the cyclometalation proceeds with Pd(II) and not with Pd(0)?
That particular reaction is Pd(II) catalyzed, not Pd(0) - JACS 1985, 107, 1781 ("A Pd(0) species such as (Ph3P)4Pd does not catalyze reaction after 12h at reflux in THF")
Related references on mechanism: JACS 1994, 116, 4255 | Acc. Chem. Res 1990, 23, 34
There are however probably similar, Pd(0)-catalyzed reactions with different conditions/ substrates (had a quick look, e.g. JOC 2004, 69, 6697)
@@totalsynthesis Thank you for your reply! Keep on making amazing content!
Mr. Woodward, you were supposed to know that!
@@jozsefszaszi355 Dear sir, me and prof. Eschenmoser are only starting to get into this novel palladium catalysis.
@Jm Cresencio that would then mean that Pd(0) is catalysing the reaction, which is the purpose of the use of Pd(OAc)2. the acetate ligands are supposed to be quite labile so they come off quite easily, allowing catalytic pathways to initiate requiring the non-complexed Pd(0). a Heck reaction is one such example of this catalytic pathway being used in synthetic application.
I clicked this knowing I wouldn’t understand a thing.. I indeed didn’t understand a single thing, but it was fun to see all those hexagons saying “Me.”
xd
It's started off good then I completely got lost 😂 I guess I'll have to do more research on synthesis before this will make since to me
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Welcome to the TH-cam graduate student seminar! I'm a biochemist with a decent organic background, and this teaches me so much. That gold-catalyzed cyclization with a cyclopropane & alkyne made my jaw drop.
Great to hear you liked it!
I AM SO HAPPY I FOUND THIS ACCOUNT. As a chemist in the drug Feild I am blow away at this synthesis. I complain at a 6 step synthesis...kudos to these nerds
Can you help me with a methoxetamine short cut? I need to get around the microwave proton rearrangement I don't have the apparatus
Stop poisoning people and give them vegetables.
nature put medicine in the food
@@obviouslytwo4u Ah yes, eating veggies will help you with TB. Truer words have never been spoken!
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me who failed chemistry 3 times: i like your funny words magic man
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Fantastic! I thoroughly enjoyed the perspective of newer total synthesis. The guys who do total syntheses these days are way past super saiyan.
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One of the most genius underrated channel on TH-cam....keep going on brother
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This is great! The only problem I can see is there's not enough content!
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Great video, I am waiting for more!! Take your time of course, is not easy to summarize a total synthesis and the target audience is very limited, but I am sure that if u keep publishing this kind of videos, all the community of synthetic organic chemist will know about you!
Hi, perhaps you will like my channel with review of selected new chemical publications. th-cam.com/users/ChemNews
so beautiful!! finally a youtube channel that really gets into the chemistry
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Coming back to this after following an organic synthesis course is very satisfying
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Wow! Very cool! Love to see a total synthesis video on youtube, and one that is very well done! Hope to see many more like this in the future!
Thanks! More in the works ;)
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I cannot understand antything but somehow it seems super interesting. Like puzzels for really intelligent people. I loved chemistry back in middle school. Shame that I lost it in the high school. It still fascinates me and I wish I could understand it.
Thanks for watching nevertheless haha
I feel very grateful to have found your channel
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Thank you for your videos, they are very interesting for an undergrad like me interested in total synthesis and retrosynthesis.
Keep up with the good work.
From Italy.
Being a synthetic chemist researcher it is quite interesting and inspiring to continue work I know that it is not easy as it seems on paper......it takes years to design such a complex synthesis
Hi, you may like my channel with review of selected new chemical publications. th-cam.com/users/ChemNews
I wanna thank the TH-cam algorithm for suggesting this to me. This is the first video I saw and its the one that made me a subscriber. as a second year chemistry student myself, I am proud to say that I understood most of what was going on.
Hi, perhaps you will like my channel with review of selected new chemical publications. th-cam.com/users/ChemNews
Please keep making videos if you can, I know TH-cam and life in general don't reward content like this much but what you do is important to get the small group of interested people to dive into this subject and potentially go on to make important discoveries.
Hi, you may like my channel with review of selected new chemical publications. th-cam.com/users/ChemNews
Hello, GREAT material with a perfectly paced delivery. Please make more videos, these are so informative and make the material much more understandable/accessible. Thank you for your patient and thoughtful insights to the chemical world!
Hi, perhaps you will like my channel with review of selected new chemical publications. th-cam.com/users/ChemNews
I'm a Bio major but I have absolutely fallen in love with Organic Chemistry; so much that I'm now a Supplemental Instructor for Orgo 2. It's just so cool!
Hi, perhaps you will like my channel with review of selected new chemical publications. th-cam.com/users/ChemNews
I've found ur channel on /sci/ months ago, had it bookmarked since then now that i got this vid recced i v become really intrigued to learn chemistry, i underwent chemotherapy and used taxol so this definitely relates to me, really appreciate the video hope to see more of
Hi, you may like my channel with review of selected new chemical publications. th-cam.com/users/ChemNews
commenting for algorithm reasons!! these videos are awesome, and im in awe at your ability to digest big papers down into an engaging format! keep it up!
Recently i studied for special methodologies in organic chemistry and i was pretty amazed when you spoke about the taxol and the background, then you procedeed to explain the synthesis...
Hi, you may like my channel with review of selected new chemical publications. th-cam.com/users/ChemNews
So glad to see a channel dedicated to recent multistep syntheses. Perfectly narrated, tho had to look up half of the name reactions
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Materials Chemist here...my mind is entirely blown apart by the retrosynthetic routes and synthesis. Holyyy.
How did you guys get good at this?
Many interesting possibilities in terms of reactions and approaches... and even more ways to "fail", leading to quite unique routes being explored
Thanks for watching!
13:50 haha that's the funniest way I've ever seen a hydration performed xD The water free hydration is brilliant.
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Great video, thanks for putting it together. Was nice to be able to recognise a lot of the transformations from my organic lectures! Modern day wizards, these guys.
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this kind of "casual" org. synth. is exactly what i needed. thanks.
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Nice video. I enjoyed learning the history as well as the organic synthesis. Subscribed-Keep up the good work!
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What a clear and lucid presentation of such a beautiful synthesis. Amazing work (both Carriera and this channel!)
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Absolutely mind blowing synthesis. Very nice video, keep up the great work!
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So helpful. This has almost every reaction from my Total Organic Synthesis class. It's like a condensed version of the Modern Organic Synthesis book by Somfai. Thank you so Much. Really interesting synthesis.
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Superb Total synthesis video. I was very excited by seeing this video. Total synthesis is good approach for applying, practicing organic reactions and retrosynthesis. Please upload more videos.
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OMG this Channel is amazing how are u still so relatively small Great work keep it up!!
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Great video! I'm glad I found your channel, I'm sure I will learn a lot. It's hard to memorise everything from such a blast of information but if you memorise one thing for each video, you will slowly be a better chemist.
Hi, perhaps you will like my channel with review of selected new chemical publications. th-cam.com/users/ChemNews
These videos are great. I wish there would me more of them! I appreaciate doing neat and nice ChemDraws such as the ones you show take time, but it is worth the effort! I would certainly spread the news of this videos to other chemists I know would enjoy!
Hi, perhaps you will like my channel with review of selected new chemical publications. th-cam.com/users/ChemNews
Currently working on my seminar presentation on the Baran lab's Taxol total synthesis route published mid 2020. It was cool watching this vid and being familiar with all of this stuff.
Hi, you may like my channel with review of selected new chemical publications. th-cam.com/users/ChemNews
Thank you for this effort!
To say well done is truly an understatement.
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Awesome video, thanks!
Glad you liked it!
Outstanding. Will be coming back when more content is posted.
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that's so beautiful
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Nice review man - tiny typo with the Bestmann reagent - there's a diazo group missing.
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This retro-synthesis is just insane.
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Through out the synthesis, bestbpart is, before disconnection, hypothetical functional group introduction -OH group like acid group on cubane and removal at end. Here did in two steps, thieves formation then treated with tin reagent. Might be can use novel methods, like triethylsilyl hydride to get product in one step to remove -OH group. Overall good lecture and I requesting you provide more and more vedios like this. Thank you.
Hi, you may like my channel with review of some selected new chemical publications. th-cam.com/users/ChemNews
This is challenging and interesting. Hope to see more. I didn't multiply the % yields but am guessing they needed a lot to start...great video.
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Since this video took you a sheetload of time to think about and make, I will honour you with a comment.
You're welcome!
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please we need more videos like this!
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Very nice Video! I even recognized some of the more "easy" steps such as the Wittig-Reaction or Ozonolysis.
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holy shit man, these are some mad organic skills. great video!
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Your content is great !Please keep on posting !
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Great video! But there is a small error. 10:58 The structure of Ohira-Bestmann reagent is incorrect. it's a diazo group at the bottom.
Thanks! Yep, I think I noted this in the description or somewhere after I realized 😇
Very interesting content. You can rarely find anything about OC in TH-cam.
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Great job! Thank you so much
Carreira is an absolute beast. I'm new to the channel and I love every bit of it
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Very well made video! I am glad i don't do total synthesis but it is super interesting to learn about
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Nice presentation! But I couldnt help but notice some mistakes. At 13:17 methyl triphenylphosphonium bromide is displayed wrong and at 14:45 there is a pentavalent carbon shown in an explanation of the NOE spectrum.
what does that mean
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THANK YOU.
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The thug glasses on E.Carreira cracked me up. Will try not to laugh when I see him in the hallway. Great video!
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Хорошее видео. Спасибо за работу, комрад)
I'd really appreciate if you discussed how advances in machine learning are contributing to advances in chemistry with specific regard to reaction prediction, synthesis analysis, pathway design etc
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amazing amount of information
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Nice video and what a beautiful synthetic approach! I have only a point of criticism: you're too fast, at least for me. I would have liked more time to look at the structures before you removed them. I know that there is a pause button, but often I had to rewind a few seconds before pausing because you have already removed them.
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Amazing video! Immediately subscribed.
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Excited to see this
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Was literally my favorite subject in graduate school. Fuck yeah.
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Listen at 1,5 times the speed and it is much more listenable :D
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One of my cohorts in my Graduate Organic synthesis class had to give a presentation on this molecule. He didn’t look like he enjoyed making the presentation though
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Lmao, poor guy
At 13:17. Is it possible that the reagent used in the Wittig-reaction should be Ph3P(+)-CH3? Otherwise, where does the Br go? In the conditions given in the publicaiton there is Ph3PCH3Br written, probably with a missing comma between the reagents Ph3P and CH3Br.
Youre right, I just copied that over without activating my brain
Great videos! I have one request, though, to make things a bit more easy to follow. Could you use a 'laser pointer' of sorts, to guide us through the molecules as you discuss them? It's sometimes kind of difficult to know which part of the molecule you're talking about, and to follow what you're saying at the same time. Especially with these complex syntheses.
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Ohira-Bestmann is a diazo carbonyl reagent.
hey i love your videos man and i would wish for some more deeper mechanisms
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How did the team manage to protect only the one of the two OH groups in the step with PivCl? Is this reaction selective or more favourable kinetic product at lower temperatures?
Yes, it's selective as the primary alcohol is more reactive than the secondary!
I LOVE your videos!!! Thank you for the content. Have you considered a different mic or audio balancing software? I’m getting a very low volume when I wtatch
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Incredible videos man!
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Awesome! You really need more views!
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HATs off for mHAT hydrofunctionalization.
I really enjoyed the retrosynthetic analysis in this video, you do a nice job addressing the issues of complexity vs accessibility in a sparsely functionalized target.
amazing video keep it up.
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Hey,
I like your approach towards each video.
here's a small detail that I would like to add according to my opinion.
It would be more engaging if you add some background music.
thank you very much.
keep up the good work. (y)
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Absolutely great video, would love to skype you and discuss some natural products and chemistry behind them. I love learning from these videos! thanks
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Please make more in depth videos like this
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More of these please
Also they should have found the gene fir this bs and over expressed it in yeast ir something
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at 11.05 min, Ohira-bestmann reagent, N2 is missing!!!
Excellent video, thanks! :)
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Danke .
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I dropped out of school a single class before my graduation. I went for chemistry but I lost interest, i didn't understand the material or how anybody could learn so many arbitrary things and pretend that they deserve to pass the class. I had passed all of my classes with at least a 3.8, and I would have probably passed this but i just hated it. I like chemistry, but school is terrible. I did not struggle with analytical chemistry, only organic. Felt like everything was completely arbitrary and based off of how well I can memorize 100 things in a single week. Not my strong suit.
Shame to hear - memorization is definitely needed for initial classes but gets better later. Hope you still enjoy chemistry to some degree!
This is amazing
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Really excellent channel. I'm quite new here, but I look forward to delving more into the channel.
I'm curious, where do you get information on things like the total sale of drugs like Taxol? I see this sort of information in papers occasionally, as a way to motivate interest in a particular compound, but I never really know where to begin looking for financial information on pharmaceutical agents that I myself am making. I hope you see this, thanks!
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What is the reason for the epimerization after treatment with the Ohira-Bestmann reagent? AFAIK, the Ohira-Bestmann reagent usually does not cause alpha epimerization, and I can't find an explanation in the paper.
Edit: I think it is due to base catalyzed alpha epimerization of the aldehyde via keto-enol tautomerism. The potassium carbonate base used with the Ohira-Bestmann reagent is able to induce keto-enol tautomerism on the aldehyde, which leads to conversion to the less sterically strained epimer.
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Eccezionale la sintesi del cubano! Ma se facciamo una nitrazione spinta, cosa otteniamo? Complimenti
Grazie
Plz upload sandal oil retrosynthesis
Great my friend!
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4:45 It's actually not the same depicted molecule. As you rightfully said it's a diastereoisomere... 😉 Greetings from another chemist. 😉 GREAT video though!
I have not worked as a chemist since I left uni 10 years ago. 😂
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Great upload thanks 😊
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Do you think snow is water or snow is water + CO2?
I'm trying to synthesize methoxetamine without the microwave proton rearrangement step. Any ideas?
Nice video,. I have one question though,, why the protected methylketone that is leading the hydroboration is pointed with dash, is a racemic micture?
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11:03 is this the correct structure of the Ohira-Bestmann reagent?
Nah I messed up mate
Brilliant
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"...thanks and have a great start to 2020..."
😂
Hi, you may like the content on my channel with review of some selected new chemistry publications. th-cam.com/users/ChemNews
Oh, I saw Me and I got confused.
My brain: that doesn't look like me.
My logic: it's probably a chemical or element.