A Convenient Synthesis of 1??Deoxy??8a??epi??Castanospermine Diastereoisomers (6R, 7R, 8S, 8aS)??6, 7, 8??Trihydroxyindolizidine and (6R, 7R, 8R, 8aS)??6, 7, 8?? …

H Zhang, YK Ni, G Zhao, Y Ding

Index: Zhang, Honglu; Ni, Yi-Ke; Zhao, Gang; Ding, Yu European Journal of Organic Chemistry, 2003 , # 10 p. 1918 - 1922

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Citation Number: 3

Abstract

Abstract An efficient synthesis of (6R, 7R, 8S, 8aS)-6, 7, 8-trihydroxyindolizidine and (6R, 7R, 8R, 8aS)-6, 7, 8-trihydroxyindolizidine is described from readily available N-BOC-L- proline,(BOC= tert-butoxycarbonyl) which involves the addition of ethyl lithiopropiolate to the aldehyde derived from N-BOC-L-proline as a key step, then cyclization to construct indolizidine skeletons and asymmetric dihydroxylation.(© Wiley-VCH Verlag GmbH & Co. ...