What a journey to put this total synthesis together. Thank you again to Jeff for providing really insightful commentary and special thank to Eleanor for joining me on this journey. Trust she has a very keen eye for synthesis!
forgot to point out you missed the alkene during steps K - L for the second synth interesting inspiration from the total synthesis of phomopsene, though I don't think it's very efficient because you built the complex carbon skeleton first with only 1-2 FGs so
Yeah missing the alkene was a typo on my part. You raise a great point. I definitely don’t think using the phomopsene synthesis to make the 5,6,5 core is “efficient”, but I thought it was fun to talk about! Jeff made a good point though too, you may be able to install functional groups earlier in the synthesis (e.g. cyclobutanone steps), but not sure how that would impact the nazarov cyclization
@@aidanlooby I do not have any idea what a carbonyl alpha to the migrating carbon could do to a carbocationic rearrangement also no other cyclic systems attached to guide diastereoselectivity I think that would be an issue
just copy from the 9th national retrosynthesis competition but invert the methyl stereocenter somehow :trol: also couldn't you do a curtius type rearrangement since the alkene was electron rich to afford the alpha amino ketone, pretty sure it's stereoretentive
What a journey to put this total synthesis together. Thank you again to Jeff for providing really insightful commentary and special thank to Eleanor for joining me on this journey. Trust she has a very keen eye for synthesis!
What about the Hofmann Löffler Freytag with the chloro imine ?
Time to add it to my named reactions tool box! 😎
forgot to point out you missed the alkene during steps K - L for the second synth
interesting inspiration from the total synthesis of phomopsene, though I don't think it's very efficient because you built the complex carbon skeleton first with only 1-2 FGs so
Yeah missing the alkene was a typo on my part. You raise a great point. I definitely don’t think using the phomopsene synthesis to make the 5,6,5 core is “efficient”, but I thought it was fun to talk about! Jeff made a good point though too, you may be able to install functional groups earlier in the synthesis (e.g. cyclobutanone steps), but not sure how that would impact the nazarov cyclization
@@aidanlooby I do not have any idea what a carbonyl alpha to the migrating carbon could do to a carbocationic rearrangement
also no other cyclic systems attached to guide diastereoselectivity I think that would be an issue
just copy from the 9th national retrosynthesis competition but invert the methyl stereocenter somehow :trol:
also couldn't you do a curtius type rearrangement since the alkene was electron rich to afford the alpha amino ketone, pretty sure it's stereoretentive
Good ppt but need some more explanation... Video is kinda rushed... Not well explained