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A Stereoselective Formal Synthesis of (−)‐Fumagillol
Author(s) -
Bedel Olivier,
Haudrechy Arnaud,
Langlois Yves
Publication year - 2004
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.200400262
Subject(s) - dihydroxylation , stereoselectivity , chemistry , fumagillin , metathesis , formal synthesis , stereochemistry , ring closing metathesis , sesquiterpene , total synthesis , enantioselective synthesis , organic chemistry , angiogenesis , catalysis , medicine , polymer , polymerization
A novel formal synthesis of fumagillol, a direct precursor of the antiangiogenic sesquiterpene fumagillin, is described. The main features of the synthesis are a stereoselective Claisen−Ireland rearrangement, a ring‐closing metathesis, a chemo‐ and stereoselective dihydroxylation, and a Julia−Kocienski olefination. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)