Tetrahedron

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

I Ojima, I Habus, M Zhao, M Zucco, YH Park, CM Sun…

文献索引：Ojima, Iwao; Habus, Ivan; Zhao, Mangzhu; Zucco, Martine; Park, Young Hoon; Sun, Chung Ming; Brigaud, Thierry Tetrahedron, 1992 , vol. 48, # 34 p. 6985 - 7012

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被引用次数: 329

摘要

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 ...