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Catalytic Enantioselective Total Syntheses of Bisorbicillinolide, Bisorbicillinol, and Bisorbibutenolide
Journal article   Peer reviewed

Catalytic Enantioselective Total Syntheses of Bisorbicillinolide, Bisorbicillinol, and Bisorbibutenolide

Ran Hong, Yonggang Chen and Li Deng
Angewandte Chemie (International ed.), Vol.44(22), pp.3478-3481
05/30/2005
PMID: 15861438

Abstract

total synthesis bisorbicillinoids rearrangement sorbicillinol Natural Products
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.

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