Helvetica chimica acta

Synthesis of (+)??(S)??Streptenol A and Biomimetic Synthesis of (2R, 4S)??and (2S, 4S)??2??(Pent??3??enyl) piperidin??4??ol

H Dollt, P Hammann, S Blechert

Index: Dollt, Heribert; Hammann, Peter; Blechert, Siegfried Helvetica Chimica Acta, 1999 , vol. 82, # 7 p. 1111 - 1121

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Citation Number: 13

Abstract

Abstract (+)-(S)-Streptenol A is synthesized by coupling a 1, 3-dithiane with an optically pure epoxide. The absolute configuration of (+)-(S)-streptenol A is thereby correlated with that of (S)-malic acid. Stereoselective reduction of an oxime that could easily be prepared from streptenol A gave the (3S, 5R)-and (3S, 5S)-aminostreptenols, and after cyclization, configurationally pure 2, 4-functionalized piperidine alkaloids.