使用临时硅连接的闭环复分解反应合成丝瓜素L和16-表丝瓜素L

Synthesis of Luffarin L and 16-epi-Luffarin L Using a Temporary Silicon-Tethered Ring-Closing Metathesis Reaction.

作者信息

Urosa Aitor, Marcos Isidro S, Díez David, Padrón José M, Basabe Pilar

机构信息

†Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos, 1-5, 37008, Salamanca, Spain.

‡BioLab, Instituto Universitario de Bio-Orgánica "Antonio González" (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna, C/Astrofísico Francisco Sánchez 2, 38206, La Laguna, Spain.

出版信息

J Org Chem. 2015 Jun 19;80(12):6447-55. doi: 10.1021/acs.joc.5b00876. Epub 2015 May 29.

DOI:10.1021/acs.joc.5b00876

PMID:25978124

Abstract

The first synthesis of luffarin L (1) and 16-epi-luffarin L (2) by a silicon-tethered ring closing metathesis as a key step has been achieved. The stereochemistry and absolute configuration of the natural sesterterpenolide luffarin L (1) and a new route for the stereoselective synthesis of sesterterpenolides with a luffarane skeleton have been established.

摘要

已实现以硅连接的闭环复分解反应为关键步骤首次合成丝瓜素L（1）和16-表丝瓜素L（2）。确定了天然倍半萜内酯丝瓜素L（1）的立体化学和绝对构型，并建立了一条立体选择性合成具有丝瓜烷骨架的倍半萜内酯的新路线。