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Synlett 1998; 1998(1): 81-83
DOI: 10.1055/s-1998-3125
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Stereoselective Synthesis of α-C-Glycopyranosyl Isoprenoid Compounds

Anne Jégou* , Carole Pacheco, Alain Veyrières
  • *Laboratoire de Synthèses et Activations de Biomolécules, CNRS ESA 6052, Ecole Nationale Supérieure de Chimie de Rennes, Campus de Beaulieu, 35700 Rennes, France; Fax +33 (2) 99 87 13 48
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Publication Date:
31 December 2000 (online)

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Addition of the allylsilane Me3SiCH2C:CH2CH2CO2Me (3) to d-gluco and d-galactopyranosyl derivatives gives in good yields 3-(α-C-glycopyranosylmethyl)-but-3-enoates which can undergo oxidation to β-ketoesters, electrophile-promoted cyclizations or double bond migration.

allylsilane - butenolides - C-glycosides - isoprenoids - β-ketoesters