阿科他他汀 A 和 B 的全合成及立体化学修订。

Total synthesis and stereochemical revision of acortatarins A and B.

机构信息

Organic Chemistry Division-II, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 607, India.

出版信息

Org Lett. 2011 Oct 21;13(20):5452-5. doi: 10.1021/ol202121k. Epub 2011 Sep 28.

DOI:10.1021/ol202121k

PMID:21955040

Abstract

A first total synthesis of acortatarins A, B, and an enantiomer of the proposed structure of acortatarin B is described by using readily available d-sugars. This convergent total synthesis revealed the revision of the absolute configuration of acortatarin A and structural revision of acortatarin B. The key steps involved are regioselective epoxide opening with deprotonated 2,5-disubstituted pyrrole and spiroketalization.

摘要

首次利用易得的 d-糖实现了 acortatarin A、B 及其假定结构的 acortatarin B 对映异构体的全合成。这种收敛性的全合成揭示了 acortatarin A 的绝对构型的修订以及 acortatarin B 的结构修订。所涉及的关键步骤包括用去质子化的 2,5-二取代吡咯进行区域选择性环氧化开环和螺缩酮化。