海葵毒素A的对映选择性全合成：一种有效的微管稳定剂。

Enantioselective total synthesis of peloruside A: a potent microtubule stabilizer.

作者信息

Ghosh Arun K, Xu Xiaoming, Kim Jae-Hun, Xu Chun-Xiao

机构信息

Departments of Chemistry and Medicinal Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.

出版信息

Org Lett. 2008 Mar 6;10(5):1001-4. doi: 10.1021/ol703091b. Epub 2008 Feb 5.

DOI:10.1021/ol703091b

PMID:18247632

Abstract

An enantioselective total synthesis of (+)-peloruside A (1) is described. Peloruside A (1) is a potent microtubule stabilizer with significant clinical potential. The synthesis is convergent and involves the assembly of C1-C10 segment 2 and C11-C24 segment 3 by a novel aldol protocol followed by Yamaguchi macrolactonization of the resulting seco-acid, selective methylation of hemi-ketal and removal of the protecting groups to peloruside A.

摘要

本文描述了(+)-海葵毒素A（1）的对映选择性全合成。海葵毒素A（1）是一种具有显著临床潜力的强效微管稳定剂。该合成是汇聚式的，包括通过一种新颖的羟醛反应方案组装C1-C10片段2和C11-C24片段3，随后对所得的半缩醛酸进行山口大环内酯化反应，对半缩酮进行选择性甲基化，并去除海葵毒素A的保护基团。