Tetrahedron

Enantioselective synthesis of (+)-kjellmanianone

…, MC Weismiller, FA Davis, D Boschelli, JR Empfield…

Index: Chen, Bang-Chi; Weismiller, Michael C.; Davis, Franklin A.; Boschelli, Diane; Empfield, James R.; Smith, Amos B. Tetrahedron, 1991 , vol. 47, # 2 p. 173 - 182

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Citation Number: 46

Abstract

An asymmetric synthesis of the highly oxygenated cyclopentanoid antibiotic (+)- kjellmanianone (1) has been achieved. The key step entailed enantioselective hydroxylation of the prochiral sodium enolate of β-keto ester 2 with the new, enantiomerically pure N- sulfonyloxaziridine 7b, affording 1 in 68.5% ee (60% yield). Possible transition state structures for the asymmetric oxidation are evaluated.