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

Damien Bourgeois (1) , Joëlle Prunet (1) , A. Pancrazi (2) , T. Prangé (3) , Jean-Yves Lallemand (1)

1 DCSO - Laboratoire de synthèse organique
2 SOSCO - Synthèse Organique Sélective et Chimie Organométallique
3 Laboratoire de Chimie Structurale Biomoléculaire

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.

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, 2000, 24, pp.4029-4036. ⟨10.1002/1099-0690(200012)2000:24<4029::AID-EJOC4029>3.0.CO;2-0⟩. ⟨hal-00954899⟩