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Total Synthesis of (+)‐Scyphostatin, a Potent and Specific Inhibitor of Neutral Sphingomyelinase
Author(s) -
Inoue Munenori,
Yokota Wakako,
Murugesh Modachur G.,
Izuhara Takashi,
Katoh Tadashi
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200454192
Subject(s) - stereocenter , stereochemistry , total synthesis , chemistry , cyclohexene , epoxide , ring (chemistry) , metathesis , negishi coupling , fatty acid , aldol reaction , side chain , amide , stereoselectivity , enantioselective synthesis , organic chemistry , catalysis , polymer , polymerization
The five crucial steps in the first total synthesis of (+)‐scyphostatin from D ‐arabinose involve (see picture): a) stereoselective aldol coupling to form a quaternary stereocenter, b) ring‐closing metathesis (RCM) to construct the cyclohexene ring, c) Negishi coupling for the preparation of the fatty acid side chain, d) amide formation to connect the cyclohexene and fatty acid segments, e) stereospecific epoxide‐ring formation.