手性选择性的贝拉酸的形式合成。

An enantioselective formal synthesis of berkelic acid.

机构信息

School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.

出版信息

Org Lett. 2011 Oct 7;13(19):5382-5. doi: 10.1021/ol202265g. Epub 2011 Sep 14.

DOI:10.1021/ol202265g

PMID:21916400

Abstract

An enantioselective formal synthesis of berkelic acid is described. The key step involves a late-stage silyl enol ether addition to a benzannulated oxonium ion with subsequent spiroketalization leading to construction of the tetracyclic core. Thermodynamically controlled equilibration under acidic conditions affords the desired spiroketal configuration as a single diastereoisomer.

摘要

本文描述了一种（手性）贝拉酸的对映选择性的形式合成方法。关键步骤包括晚期的硅基烯醇醚对苯并环化的氧鎓离子的加成，随后的螺缩酮化导致四环核心的构建。在酸性条件下的热力学控制平衡以单一非对映异构体的形式提供所需的螺缩酮构型。