从少花麻风树中分离出的罕见倍半萜类化合物的立体选择性全合成。

Stereoselective total syntheses of uncommon sesquiterpenoids isolated from Jatropha neopauciflora.

作者信息

Hayashi Yujiro, Miyakoshi Naoki, Kitagaki Shinji, Mukai Chisato

机构信息

Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-Machi, Kanazawa, Japan.

出版信息

Org Lett. 2008 Jun 19;10(12):2385-8. doi: 10.1021/ol800633a. Epub 2008 May 14.

DOI:10.1021/ol800633a

PMID:18476710

Abstract

The first total syntheses of two tricyclic sesquiterpenes 1 and 2, isolated from Jatropha neopauciflora, were completed from dimethyl D-tartrate in a stereoselective manner. The crucial steps in these syntheses involved not only the Rh(I)-catalyzed Pauson-Khand-type reaction of the allenene derivative leading to the exclusive formation of the bicyclo[4.3.0]nonenone framework possessing an angular methyl group but also a highly stereoselective construction of the isopropylcyclopropane ring.

摘要

从少花麻风树中分离得到的两种三环倍半萜1和2的首次全合成以立体选择性的方式由D - 酒石酸二甲酯完成。这些合成中的关键步骤不仅涉及铑（I）催化的丙二烯衍生物的Pauson - Khand型反应，该反应导致具有角甲基的双环[4.3.0]壬烯酮骨架的唯一形成，还涉及异丙基环丙烷环的高度立体选择性构建。