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Catalytic Enantioselective Total Syntheses of Bisorbicillinolide, Bisorbicillinol, and Bisorbibutenolide


  • This work was financially supported by the National Institutes of Health (GM-61591).


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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.