Helvetica chimica acta

Total Synthesis of (2Z)??[(4R, 5R, 6S)??6??(β??D??Glucopyranosyloxy)??4, 5??dihydroxycyclohex??2??en??1??ylidene] ethanenitrile, a Cyanoglucoside from Ilex warburgii

D Josien??Lefebvre, C Le Drian

Index: Josien-Lefebvre, Delphine; Le Drian, Claude Helvetica Chimica Acta, 2007 , vol. 90, # 1 p. 19 - 30

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Abstract

Abstract The total synthesis of the noncyanogenic cyanoglucoside 1, originally isolated from Ilex warburgii, was achieved in nine steps (9% overall yield), starting from an optically pure Diels–Alder adduct ((+)-3). The key step of the synthesis, the glycosidation, was carried out under Koenigs–Knorr conditions closely related to those developed for the total syntheses of (−)-lithospermoside and (−)-bauhinin. We had to tune the protecting groups used for the ...