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First Total Synthesis of (+)‐Adenophorine, a Naturally Occurring Inhibitor of Glycosidases
Author(s) -
Pearson Morwenna S. M.,
Evain Michel,
MathéAllainmat Monique,
Lebreton Jacques
Publication year - 2007
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.200700459
Subject(s) - chemistry , iminosugar , aldehyde , hydroxymethyl , enantiomer , total synthesis , stereochemistry , enantioselective synthesis , surface modification , organic chemistry , combinatorial chemistry , enzyme , catalysis
The first total synthesis of a naturally occurring iminosugar, (+)‐adenophorine, in 14 steps from the (+)‐enantiomer ofGarner's aldehyde, is reported. The strategy is based onthe preparation and functionalization of enantiomericallypure trans ‐6‐ethyl‐2‐hydroxymethyl‐1,2,5,6‐tetrahydropyridine. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)