（+）-香叶基异氰酸酯的不对称合成：绝对立体化学的确定。

Asymmetric synthesis of (+)-geranyllinaloisocyanide: assignment of absolute stereochemistry.

机构信息

Faculty of Science, Kochi University, Akebono-cho, Kochi, Japan.

出版信息

Org Lett. 2011 May 20;13(10):2520-3. doi: 10.1021/ol200308m. Epub 2011 Apr 14.

DOI:10.1021/ol200308m

Abstract

The first nonracemic synthesis of (+)-geranyllinaloisocyanide, starting with (-)-lactic acid methyl ester, has been accomplished by exploiting a [3.3] sigmatropic rearrangement of allyl cyanate. The synthesis enables assignment of the S configuration of the C(3) isocyano substituted, quaternary stereogenic center in natural geranyllinaloisocyanide.

摘要

首次采用[3.3]σ重排反应，以（-）-乳酸甲酯为起始原料，完成了（+）-香叶基异氰酸酯的非对映体全合成。该合成方法可确定天然香叶基异氰酸酯中 C(3)位取代的、季碳手性中心的 S 构型。