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

Authors
Bourgeois, D Prunet, J Pancrazi, A Prange, T Lallemand, JY
Citation
D. Bourgeois et al., Alkyne zip reaction in the synthesis of a taxoid C-ring, EUR J ORG C, (24), 2000, pp. 4029-4036
Citations number
31
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
24
Year of publication
2000
Pages
4029 - 4036
Database
ISI
SICI code
1434-193X(200012):24<4029:AZRITS>2.0.ZU;2-T
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' yea st to introduce enantioselectivity. During the alkyne isomerization step, a nionic cyclizations of alkoxides and enolates onto the triple bond were obs erved, and a thorough study of these reactions is reported here.