一种用于制霉素四环核心的便捷对映选择性策略。

An expedient enantioselective strategy for the oxatetracyclic core of platensimycin.

作者信息

Kaliappan Krishna P, Ravikumar Velayutham

机构信息

Department of Chemistry, Indian Institute of Technology-Bombay, Powai, Mumbai, India.

出版信息

Org Lett. 2007 Jun 7;9(12):2417-9. doi: 10.1021/ol070848t. Epub 2007 May 10.

DOI:10.1021/ol070848t

PMID:17489601

Abstract

An enantioselective route for the synthesis of oxatetracyclic core of platensimycin is reported for the first time using a 5-exo-trig cyclization followed by intramolecular etherification as key reactions. The requisite dienynone for the radical cyclization is synthesized in eight steps from the Wieland-Miescher ketone employing a Claisen rearrangement.

摘要

首次报道了一条对映选择性合成普拉特烯霉素氧杂四环核心的路线，该路线以5-外向-三取代环化反应和分子内醚化反应作为关键反应。用于自由基环化的必需二烯炔酮由维兰德-米舍尔酮经克莱森重排反应分八步合成。