The Journal of Organic Chemistry

Enantioselective synthesis of seven pyrrolizidine diols from a single precursor

AR Chamberlin, JYL Chung

Index: Chamberlin, A. Richard; Chung, John Y. L. Journal of Organic Chemistry, 1985 , vol. 50, # 23 p. 4425 - 4431

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Citation Number: 59

Abstract

The enantioselective synthesis of seven pyrrolizidine diols has been accomplished from a single, readily available intermediate. The key step of this general scheme involves an acetoxy-directed acyliminium ion-ketene dithioacetal cationic cyclization to give the optically active l-azabicyclo [3.3. 0] octane 14, from which the pyrrolizidines 1-7 were prepared. The pyrrolizidine diols in the 7s series were obtained by adjusting the oxidation level and ...