立体选择性缩酮连接的分子内狄尔斯-阿尔德环加成反应。一种构建抗真菌剂夫西地内酯C的2-氧杂十氢化萘螺缩酮核心的方法。

Stereoselective ketal-tethered intramolecular diels-alder cycloadditions. An approach to the 2-oxadecalin spiroketal core of antifungal agent fusidilactone C.

作者信息

Wang Jiashi, Hsung Richard P, Ghosh Sunil K

机构信息

Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.

出版信息

Org Lett. 2004 Jun 10;6(12):1939-42. doi: 10.1021/ol0495624.

DOI:10.1021/ol0495624

PMID:15176788

Abstract

[reaction: see text] An approach toward the 2-oxadecalin spiroketal core of fusidilactone C via a rare ketal-tethered intramolecular Diels-Alder cycloaddition is described here. This intramolecular Diels-Alder cycloaddition is highly endo-selective and overall depended upon the nature of solvents and Lewis acids. We also observed some remarkable rate acceleration in MeOH.

摘要

[反应：见正文] 本文描述了一种通过罕见的缩酮连接的分子内狄尔斯-阿尔德环加成反应构建夫西地内酯C的2-氧杂十氢化萘螺缩酮核心的方法。这种分子内狄尔斯-阿尔德环加成反应具有高度的内型选择性，并且总体上取决于溶剂和路易斯酸的性质。我们还观察到在甲醇中反应速率有显著加快。