Stereoselective Syntheses of Ethyl (Z)-  and (E)-Octa-2,6-dienopyranosiduronates from  Ethyl 2,3-Dideoxy-α-D-erythro-hex-2-enopyranoside

Ana M. Gómez; J. Cristóbal López; Bert Fraser-Reid

doi:10.1055/s-1993-22527

Synlett 1993; 1993(8): 557-560
DOI: 10.1055/s-1993-22527

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Stereoselective Syntheses of Ethyl (Z)- and (E)-Octa-2,6-dienopyranosiduronates from Ethyl 2,3-Dideoxy-α-D-erythro-hex-2-enopyranoside

Ana M. Gómez^* , J. Cristóbal López, Bert Fraser-Reid

^*Paul M. Gross Chemical Laboratory, Department of Chemistry, Duke University, Durham, NC 27708, USA

Abstract

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(Z)- and (E)- isomers of oct-2,6-dienopyranosiduronates have been synthesized in a completely stereoselective manner from ethyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside. The selectivity of the processes is dictated by an unexpected opposite stereochemical behavior towards stabilized Wittig ylides of protected and unprotected 4-hydroxy derivatives in hex-2-enopyranoside-6-aldehydes.

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