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Semisynthesis of Taxol: A Highly Enantio‐ and Diastereoselective Synthesis of the Side Chain and a New Method for Ester Formation at C13 Using Thioesters
Author(s) -
Gennari Cesare,
Vulpetti Anna,
Donghi Monica,
Mongelli Nicola,
Vanotti Ermes
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199617231
Subject(s) - semisynthesis , thioester , acylation , chemistry , side chain , terpene , stereochemistry , imine , absolute configuration , yield (engineering) , combinatorial chemistry , organic chemistry , enzyme , polymer , materials science , metallurgy , catalysis
The production of Paclitaxel (taxol, 2) on an industrial scale may be possible with a novel semisynthesis relying on the readily accessible 10‐deacetylbaccatin III and the side‐chain unit 1 . The crucial factor is the remarkably high yield for the 13‐O‐acylation of the terpene framework, which is usually very difficult. Thioester 1 can be prepared fairly directly with the desired relative and absolute configuration by addition of the appropriate boron enolate to an imine.