Catalytic Enantioselective Total Syntheses of Bisorbicillinolide, Bisorbicillinol, and Bisorbibutenolide

Abstract

A modified cinchona alkaloid catalyzed ketone cyanosilylation reaction is used as the stereochemistry-defining step in the total synthesis of sorbicillinol derivatives (a protected derivative is shown (PMB=para-methoxybenzyl)). These enantioselective total syntheses were accomplished in 10/11 steps and 12–19 % overall yields. Furthermore, the chemical conversion of bisorbicillinol into bisorbicillinolide provides insight into the biosynthesis of bisorbicillinolide. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z500480_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.