鼠索林的首次全合成。

First total synthesis of murisolin.

作者信息

Maezaki Naoyoshi, Tominaga Hiroaki, Kojima Naoto, Yanai Minori, Urabe Daisuke, Tanaka Tetsuaki

机构信息

Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.

出版信息

Chem Commun (Camb). 2004 Feb 21(4):406-7. doi: 10.1039/b312362f. Epub 2004 Jan 19.

DOI:10.1039/b312362f

PMID:14765231

Abstract

The first and concise total synthesis of murisolin (1) was accomplished using asymmetric alkynylation and Sonogashira coupling as the key steps. The threo/trans/threo-type THF ring moiety was constructed with excellent stereoselectivity by asymmetric alkynylation of 1,6-heptadiyne to alpha-tetrahydrofuranic aldehyde, which was also prepared via the asymmetric alkynylation.

摘要

利用不对称炔基化反应和Sonogashira偶联反应作为关键步骤，首次实现了对鼠李素（1）的简洁全合成。通过1,6-庚二炔对α-四氢呋喃醛进行不对称炔基化反应，以优异的立体选择性构建了苏式/反式/苏式型四氢呋喃环部分，而α-四氢呋喃醛也是通过不对称炔基化反应制备的。