(-)-连翘脂素 A 的对映选择性合成的改进：芳基-Csp(3)键的受阻旋转。

Improved enantioselective synthesis of (-)-linderol A: hindered rotation about aryl-Csp(3) bond.

机构信息

Institut de Chimie Moléculaire de Reims, CNRS UMR 6229, Université de Reims Champagne-Ardenne, Faculté de Pharmacie, 51 rue Cognacq-Jay, F-51096 Reims Cedex, France.

出版信息

J Org Chem. 2010 Apr 16;75(8):2501-9. doi: 10.1021/jo902567y.

DOI:10.1021/jo902567y

PMID:20334420

Abstract

An improved enantioselective total synthesis of (-)-linderol A has been achieved via a five-step reaction with a 21% overall yield, starting from phloroacetophenone and (-)-alpha-phellandrene, two commercially available reagents. In the diastereoselective epoxidation step, the analysis of the two endocyclic epoxide intermediates reveals a hindered sp(2)-sp(3) rotation, which results in rotational diastereoisomers.

摘要

一种改进的 (-)-缬草醇 A 的对映选择性全合成已经通过从商业可得的试剂 phloroacetophenone 和 (-)-alpha-phellandrene 出发的五步反应以 21%的总收率实现。在非对映选择性环氧化步骤中，两个内环氧中间体的分析揭示了受阻的 sp(2)-sp(3)旋转，导致旋转非对映异构体。