A PRACTICAL ACCESS TO CHIRAL PHENYLISOSERINATES, PREPARATION OF TAXOTERE(R) ANALOGS

Authors
BOURZAT JD COMMERCON A
Citation
Jd. Bourzat et A. Commercon, A PRACTICAL ACCESS TO CHIRAL PHENYLISOSERINATES, PREPARATION OF TAXOTERE(R) ANALOGS, Tetrahedron letters, 34(38), 1993, pp. 6049-6052
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
38
Year of publication
1993
Pages
6049 - 6052
Database
ISI
SICI code
0040-4039(1993)34:38<6049:APATCP>2.0.ZU;2-5
Abstract
A practical diastereoselective synthesis of phenylisoserine methyl est ers 8a-c is described using alpha-methyl-benzylamine as the chiral tem plate of a Staudinger reaction. Optically pure diastereoisomers 6a-c w ere easily recovered by crystallization. After opening of these interm ediate azetidinones by hydrochloric acid and methanol, regioselective cleavage of the chiral auxiliary was achieved by hydrogenation over pa lladium. Phenylisoserinates 8b,c were used to prepare analogs of Taxot ere(R).