金催化的分子内串联亲电加成和苯并环化反应合成芳基萘木脂素骨架。

Synthesis of arylnaphthalene lignan scaffold by gold-catalyzed intramolecular sequential electrophilic addition and benzannulation.

机构信息

School of Chemistry, University of Hyderabad, Gachibowli, Hyderabad 500046, India.

出版信息

J Org Chem. 2011 Dec 16;76(24):9919-33. doi: 10.1021/jo201918d. Epub 2011 Nov 14.

DOI:10.1021/jo201918d

PMID:22029795

Abstract

An intramolecular approach to generate compounds containing an arylnaphthalene lignan scaffold in high yields is presented. It involves a sequential intramolecular electrophilic attack of carbonyl on arylalkyne followed by benzannulation catalyzed by gold salt. AuCl(3) in combination with AgSbF(6) works better to effect this transformation. Selected products have been converted into arylnaphthalene lactone natural products such as justicidin E, taiwanin C, and retrojusticidin B.

摘要

本文提出了一种高产率合成含芳基萘烷木脂素骨架化合物的分子内方法。它涉及羰基对芳基炔烃的顺序分子内亲电攻击，然后在金盐催化下进行苯并环化。AuCl(3)与 AgSbF(6)的组合更有利于实现这种转化。选择的产物已转化为芳基萘烷内酯天然产物，如 justicidin E、taiwanin C 和 retrojusticidin B。