A Stereoselective Formal Synthesis of (−)‐Fumagillol | Zendy

Bedel Olivier | Zendy; Haudrechy Arnaud | Zendy; Langlois Yves | Zendy

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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)

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