Stereoselective synthesis of bicyclo[4.2.1]nonane skeletons by ring-closing metathesis: a new versatile methodology for the efficient assembly of functionalized cyclooctanoids.
[reaction: see text] A new versatile methodology, resulting in a formal three-carbon ring expansion of cyclopentanones, for the efficient assembly of functionalized cyclooctanoids is described. The approach is based on the chemo-, regio-, and stereoselective alpha,gamma-difunctionalization of beta-ketoesters followed by ring-closing metathesis to form functionalized bicyclo[4.2.1]nonanes, precursors of the corresponding cyclooctanes, by selective ring cleavage of the one-carbon-atom bridge.
Michaut
Antoine
A
Université Paul Cézanne, (U-III), UMR-CNRS-6178-SymBio, Equipe RéSo, Réactivité en Synthèse organique, Centre de St Jérôme, boîte D12, 13397 Marseille Cedex 20, France.
Miranda-Garcia
Sonia
S
Menéndez
J Carlos
JC
Rodriguez
Jean
J