一种系链控制的外向选择性跨环狄尔斯-阿尔德（TADA）反应。

A tether controlled exo-selective trans-annular Diels-Alder (TADA) reaction.

作者信息

Felzmann Wolfgang, Arion Vladimir B, Mieusset Jean-Luc, Mulzer Johann

机构信息

Institut für Organische Chemie, Universität Wien, Währingerstrasse 38, A-1090 Vienna, Austria.

出版信息

Org Lett. 2006 Aug 17;8(17):3849-51. doi: 10.1021/ol061510m.

DOI:10.1021/ol061510m

PMID:16898833

Abstract

[reaction: see text] A fully substrate controlled stereoselective route to construct cis-hexahydronaphthalene 4 is described starting from nonracemic butenolide 6. The key step is an exo-selective transannular Diels-Alder reaction (TADA) of tetraene 5, whose intrinsic constraint allows selective formation of one stereodefined product. Compound 4 is a key intermediate in the synthesis of the novel antibiotic branimycin (1).

摘要

[反应：见正文] 描述了一条从非外消旋丁烯内酯6出发构建顺式六氢萘4的完全受底物控制的立体选择性路线。关键步骤是四烯5的外式选择性跨环狄尔斯-阿尔德反应（TADA），其内在限制允许选择性地形成一种立体构型确定的产物。化合物4是新型抗生素布拉霉素（1）合成中的关键中间体。