- Transition-metal-free stereoselective synthesis of C(1)–C(6) fragment of epothilones and their structural analogues
-
Two efficient and scalable asymmetric syntheses of C(1)–C(6) fragment of epothilones and their structural analogues from commercially available 1,2:5,6-di-O-isopropylidene-D-mannitol have been performed in seven and 12 steps with 35% and 36% overall yields, respectively. Both the approaches include of one-pot, sequential transformations. The key steps are L-histidine-catalyzed aldol reaction, Barton–McCombie deoxygenation, zinc-mediated Vasella fragmentation, and oxidative nitrile synthesis.
- Shklyaruck, Denis G.,Fedarkevich, Artsiom N.,Kozyrkov, Yurii Yu.
-
p. 8015 - 8021
(2016/11/22)
-
- Anionic reactions of N-(trans-2,3-diphenylaziridin-1-yl)imines and their use as 1,1-dipoles in anionic cyclizations
-
Reaction of N-(trans-2,3-diphenylaziridin-1-yl)imines with alkyllithiums and organocuprates afforded the desired addition products after consecutive fragmentations along with liberation of stilbene and nitrogen gas, while the reaction of N-(2-phenylaziridin-1-yl)imines under similar conditions gave an anomalous by-product. Anionic cyclizations of N-(trans-2,3-diphenylaziridin-1- yl)imines using unactivated alkenes and alkynes as acceptors proceeded smoothly, yielding cyclized products in good yields.
- Hwang, Jung-Il,Hong, Young-Taek,Kim, Sunggak
-
p. 1513 - 1516
(2007/10/03)
-