Tetrahedron p. 2805 - 2828 (1993)
Update date:2022-08-02
Topics:
Chen, Shu-Hui
Huang, Stella
Wei, Jianmei
Farina, Vittorio
Several Lewis acids were shown to cleanyl open the oxetane ring of taxol and baccatin derivatives.The reaction is shown to proceed via anchimeric assistance by the C-4 acetate group.Several minor products, including a novel derivative possessing a bridged C-ring, were also isolated.A mechanistric rationale is provides for all compounds formed.When taxol derivatives were treated with Lewis acids in methanol, ester cleavage reactions were observed.We provide conditions that are selective for C-10 acetate cleavage and for C-13 side-chain methanolysis.
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Doi:10.1016/S0040-4039(00)77630-1
(1993)Doi:10.1002/jhet.5570290509
(1992)Doi:10.1016/S0960-894X(01)00330-4
(2001)Doi:10.1016/S0957-4166(00)86295-3
(1994)Doi:10.1021/jo00068a056
(1993)Doi:10.1021/jo00070a049
(1993)
