Direct Access to Furanosidic Eight??Membered Ulosonic Esters from cis?螃?, β??Epoxy Aldehydes

CH Sugisaki, Y Ruland, M Baltas

Index: Sugisaki, Claudia H.; Ruland, Yvan; Baltas, Michel European Journal of Organic Chemistry, 2003 , # 4 p. 672 - 688

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Citation Number: 14

Abstract

Abstract Direct access to bicyclic precursors of octulosonic acids is achieved by treatment of differentially (or not) protected γ, δ-bis (silyloxy) cis-α, β-epoxy aldehydes with ethyl 2- (trimethylsilyloxy)-2-propenoate in the presence of boron trifluoride− diethyl ether. An X-ray crystallographic structure of a bicycle (compound 33a) was obtained and used to determine the absolute configurations of the different stereogenic centers and thus the ...

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