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Total Synthesis of Epothilone E and Analogues with Modified Side Chains through the Stille Coupling Reaction
Author(s) -
Nicolaou K. C.,
He Yun,
Roschangar Frank,
King N. Paul,
Vourloumis Dionisios,
Li Tianhu
Publication year - 1998
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/(sici)1521-3773(19980202)37:1/2<84::aid-anie84>3.0.co;2-v
Subject(s) - stille reaction , epothilone , epothilones , salt metathesis reaction , side chain , chemistry , stereochemistry , metathesis , olefin metathesis , combinatorial chemistry , organic chemistry , catalysis , polymer , polymerization
Ring‐closing metathesis (step a in the scheme below), deprotection (b), Stille coupling (c), and epoxidation (d) are the key steps in the first total synthesis of the naturally occurring epothilone E ( 1 ). An advanced intermediate, the product of the olefin metathesis, allows access to a range of epothilone E analogues having different aromatic moieties in the side chain. TBS = t BuMe 2 Si.