First Total Synthesis of (+)‐Adenophorine, a Naturally Occurring Inhibitor of Glycosidases | Zendy

Pearson Morwenna S. M. | Zendy; Evain Michel | Zendy; MathéAllainmat Monique | Zendy; Lebreton Jacques | Zendy

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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)

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