串联氧化去芳构化/分子内 Diels-Alder 反应构建 palhinine A 的三环核心。

Tandem oxidative dearomatization/intramolecular Diels-Alder reaction for construction of the tricyclic core of palhinine A.

机构信息

State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.

出版信息

Org Lett. 2012 May 4;14(9):2293-5. doi: 10.1021/ol3007138. Epub 2012 Apr 12.

DOI:10.1021/ol3007138

PMID:22497445

Abstract

A concise construction of the 6/6/5 tricyclic core of Lycopodium alkaloid palhinine A (1) has been accomplished. The developed synthetic strategy featured a tandem oxidative dearomatization/intramolecular Diels-Alder reaction to construct C/D rings and an intramolecular 5-exo-trig radical cyclization to install the B ring of palhinine A (1). The developed approach paves the way for the total synthesis of palhinine A (1).

摘要

已经完成了石松生物碱 palhinine A（1）的 6/6/5 三环核心的简洁构建。所开发的合成策略的特点是串联氧化去芳构化/分子内 Diels-Alder 反应构建 C/D 环和分子内 5-endo-三键自由基环化以安装 palhinine A（1）的 B 环。所开发的方法为 palhinine A（1）的全合成铺平了道路。