Alkyne zip reaction in the synthesis of a taxoid C-ring

Abstract : Hydrazone 30, precursor of a taxoid C-ring, was synthesized in 7 steps from commercial 2-methyl-1,3-cyclohexanedione. An enantioselective approach to 30 was also investigated, using a reduction of diketone 11 with bakers' yeast to introduce enantioselectivity. During the alkyne isomerization step, anionic cyclizations of alkoxides and enolates onto the triple bond were observed, and a thorough study of these reactions is reported here. © Wiley-VCH Verlag GmbH, 2000.
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Damien Bourgeois, Joëlle Prunet, A. Pancrazi, T. Prangé, Jean-Yves Lallemand. Alkyne zip reaction in the synthesis of a taxoid C-ring. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2000, pp.4029-4036. ⟨10.1002/1099-0690(200012)2000:24<4029::AID-EJOC4029>3.0.CO;2-0⟩. ⟨hal-00954899⟩

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