立体选择性合成 3-芳基八氢吲哚及其在（-）-pancracine 全合成中的应用。

Stereoselective synthesis of 3-aryloctahydroindoles and application in a formal synthesis of (-)-pancracine.

机构信息

Department of Chemistry, Memorial University, St. John's, Newfoundland, Canada A1B 3X7.

出版信息

Org Lett. 2010 Feb 5;12(3):556-9. doi: 10.1021/ol902761a.

PMID:20055457

Abstract

A stereoselective synthesis of 3-aryloctahydroindoles from enantiomerically enriched gamma-nitroketones has been developed. Reduction of imines derived form the nitroketones provides the trans-fused octhaydroindole motif selectively. The cis-octahydroindole skeleton is accessible by an invertive cyclization strategy involving a diastereomerically pure nitromesylate intermediate. This approach was employed in the synthesis of an advanced intermediate to (-)-pancracine. The gamma-nitroketone starting materials are readily available via an organocatalytic Michael reaction.

摘要

已开发出一种对映体富集的γ-硝基酮的 3-芳基八氢吲哚的立体选择性合成方法。从硝基酮衍生的亚胺的还原选择性地提供了顺式稠合八氢吲哚基序。通过涉及立体纯的硝甲酯中间体的反转环化策略，可以获得顺式八氢吲哚骨架。该方法用于合成（-）-pancracine 的高级中间体。γ-硝基酮起始物料可通过有机催化的迈克尔反应轻松获得。