首次对 (+)-neovibsanin B 进行对映选择性的全合成， (+)-neovibsanin B 是一种具有神经营养作用的二萜。

First enantiocontrolled formal synthesis of (+)-neovibsanin B, a neurotrophic diterpenoid.

机构信息

Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.

出版信息

Org Lett. 2010 Feb 19;12(4):888-91. doi: 10.1021/ol902960n.

PMID:20092277

Abstract

An enantiocontrolled formal synthesis of (+)-neovibsanin B has been achieved by a sequence that applies an asymmetric 1,4-addition of (H(2)C=CH)(2)Cu(CN)Li(2) to trisubstituted alpha,beta-carboxylic acid derivative 1 to induce the chirality at the C-11 all-carbon quaternary center. Together with a modified Negishi cyclic carbopalladation-carbonylative esterification tandem reaction for constructing the A-ring, the synthesis was completed.

摘要

通过一个序列实现了（+）-neovibsanin B 的对映选择性全合成，该序列应用不对称的 1,4-加成（H(2)C=CH)(2)Cu(CN)Li(2) 到三取代的 α,β-羧酸衍生物 1 上，诱导 C-11 全碳季碳中心的手性。与用于构建 A 环的改良 Negishi 环碳钯化-羰基酯化串联反应一起，完成了合成。