通过迭代双羟基化序列对10-表阿那马林进行对映选择性合成。

Enantioselective synthesis of 10-epi-anamarine via an iterative dihydroxylation sequence.

作者信息

Gao Dong, O'Doherty George A

机构信息

Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.

出版信息

Org Lett. 2005 Mar 17;7(6):1069-72. doi: 10.1021/ol047322i.

DOI:10.1021/ol047322i

PMID:15760141

Abstract

[reaction: see text] The enantioselective syntheses of 10-epi-anamarine and 5,10-epi,epi-anamarine have been achieved in 13 to 14 steps. The route relies upon an enantio- and regioselective Sharpless dihydroxylation of either dienoates or trienoates to establish the C-8 to C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route also relies upon a ring-closing metathesis to establish the alpha,beta-unsaturated lactones.

摘要

[反应：见正文] 已通过13至14步实现了10-表阿那马林和5,10-表，表阿那马林的对映选择性合成。该路线依赖于二烯酸酯或三烯酸酯的对映和区域选择性夏普莱斯双羟基化反应来确定C-8至C-11的立体化学。非对映选择性的莱顿烯丙基化反应确定了所需的C-5立体化学。该路线还依赖于关环复分解反应来构建α,β-不饱和内酯。