Efficient and Practical Asymmetric Synthesis of the Taxol C-13 Side Chain, N-Benzoyl-(2R,3S)-3-phenylisoserine, and Its Analogues via Chiral 3-Hydroxy-4-aryl-β-lactams through Chiral Ester Enolate–Imine Cyclocondensation

Iwao Ojima, Ivan Habus, Mangzhu Zhao, Gunda I. Georg, Lalith R. Jayasinghe

Research output: Contribution to journalArticlepeer-review

218 Scopus citations

Abstract

A highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with >96% ee is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenylisoserine, and its analogues.

Original languageEnglish (US)
Pages (from-to)1681-1683
Number of pages3
JournalJournal of Organic Chemistry
Volume56
Issue number5
DOIs
StatePublished - Mar 1 1991

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