Nakamura S, Inagaki J, Sugimoto T, Kudo M, Nakajima M, Hashimoto S
Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.
Org Lett. 2001 Dec 13;3(25):4075-8. doi: 10.1021/ol0168364.
[reaction: see text] An efficient synthesis of the C10-C31 (BCDEF ring) portion of pinnatoxin A has been achieved. The key step is a highly stereoselective construction of the dispiroketal (BCD ring) system employing an intramolecular hetero-Michael reaction of a reversibly formed hemiketal alkoxide through the use of LiOMe.
[反应：见正文] 已实现了海葵毒素A的C10-C31（BCDEF环）部分的高效合成。关键步骤是通过使用LiOMe，利用可逆形成的半缩醛醇盐的分子内杂迈克尔反应，高度立体选择性地构建双螺缩酮（BCD环）体系。
