通过非对映体拆分-选择性脱保护来开发具有双环[3.3.0]辛烷骨架的手性砌块。

Development of chiral building blocks having a bicyclo[3.3.0]octane framework using a diastereomeric resolution-selective deprotection.

作者信息

Tamura Masafumi, Oyamada Miki, Shirataki Yoshiaki

机构信息

Faculty of Pharmaceutical Sciences, Josai University, Saitama, Japan.

出版信息

Chirality. 2015 Jun;27(6):364-9. doi: 10.1002/chir.22450. Epub 2015 Apr 23.

DOI:10.1002/chir.22450

PMID:25908334

Abstract

A protocol is presented for an efficient and practical approach to the synthesis of enantiomerically pure bicyclo[3.3.0]octane derivatives from achiral Cs-symmetric bicyclo[3.3.0]octane-2,8-dione using a diastereomeric resolution-selective deprotection method. This method affords chiral building blocks having bicyclo[3.3.0]octane framework with the same site of diastereotopic carbonyl functional group.

摘要

本文介绍了一种通过非对映体拆分-选择性脱保护方法，从非手性的Cs对称双环[3.3.0]辛烷-2,8-二酮高效实用地合成对映体纯双环[3.3.0]辛烷衍生物的方案。该方法提供了具有双环[3.3.0]辛烷骨架且非对映异位羰基官能团位于相同位置的手性结构单元。