New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method

Iwao Ojima*, Ivan Habus, Mangzhu Zhao, Martine Zucco, Young Hoon Park, Chung-Ming Sun, Thierry Brigaud

*Corresponding author for this work

Research output: Contribution to journalArticle

314 Scopus citations

Abstract

Highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with excellent enantiomeric purity is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenyl-isoserine and its analogs. (3R,4S)-N-benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone readily derived from the 3-hydroxy-4-phenyl-β-lactam is coupled with protected baccatin IIIs, followed by deprotection to give optically pure taxol and 10-deacetyl-7,10-bis(Troc)-taxol in good yields. Fully assigned 1H, 13C, and 2D (COSY and HETCOR) NMR spectra of taxol thus synthesized are shown and discussed.

Original languageEnglish
Pages (from-to)6985-7012
Number of pages28
JournalTetrahedron
Volume48
Issue number34
DOIs
StatePublished - 1 Jan 1992

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