肿瘤及糖原合成酶激酶-3β抑制性生物碱（-）-agelastatin A的对映体特异性形式全合成。

Enantiospecific formal total synthesis of the tumor and GSK-3 beta inhibiting alkaloid, (-)-agelastatin A.

作者信息

Hale Karl J, Domostoj Mathias M, Tocher Derek A, Irving Ed, Scheinmann Feodor

机构信息

The Christopher Ingold Laboratories, University College London, 20 Gordon Street, London WC1H 0AJ, England.

出版信息

Org Lett. 2003 Aug 7;5(16):2927-30. doi: 10.1021/ol035036l.

DOI:10.1021/ol035036l

PMID:12889910

Abstract

[reaction: see text] An enantiospecific total synthesis of Weinreb's advanced intermediate 2 for (-)-agelastatin A has been achieved from the Hough-Richardson aziridine 8. Noteworthy reactions in our sequence include the highly regioselective trans-diaxial ring-opening of 8 with azide ion to set up the vicinal diamido functionality present within (-)-2 and the Grubbs-Hoveyda ring-closing metathesis (RCM) reaction that was used to construct its cyclopentene core.

摘要

[反应：见正文] 已从霍夫-理查森氮丙啶8实现了对（-）-阿吉拉他汀A的温雷布高级中间体2的对映体特异性全合成。我们合成路线中值得注意的反应包括8与叠氮离子的高度区域选择性反式双轴开环反应，以建立（-）-2中存在的邻位二酰胺官能团，以及用于构建其环戊烯核心的格拉布-霍维达闭环复分解（RCM）反应。