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A Convenient Synthesis of 1‐Deoxy‐8a‐ epi ‐Castanospermine Diastereoisomers (6 R ,7 R ,8 S ,8a S )‐6,7,8‐Trihydroxyindolizidine and (6 R ,7 R ,8 R ,8a S )‐6,7,8‐Trihydroxyindolizidine
Author(s) -
Zhang Honglu,
Ni YiKe,
Zhao Gang,
Ding Yu
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200200412
Subject(s) - chemistry , dihydroxylation , indolizidine , diastereomer , castanospermine , stereochemistry , aldehyde , proline , enantioselective synthesis , organic chemistry , amino acid , enzyme , catalysis , biochemistry , alkaloid
An efficient synthesis of (6 R ,7 R ,8 S ,8a S )‐6,7,8‐trihydroxyindolizidine and (6 R ,7 R ,8 R ,8a S )‐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. KGaA, 69451 Weinheim, Germany, 2003)