Sugar enolones, XIX. An approach to actinospectose??type 2, 3??diketo sugars.–Synthetic proof for the R configuration of “Herzgift??Methylreduktinsäure”

FW Lichtenthaler, A Löhe…

Index: Lichtenthaler, Frieder W.; Loehe, Albert; Cuny, Eckehard Liebigs Annalen der Chemie, 1983 , # 11 p. 1973 - 1985

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Abstract

Abstract A stereochemically defined, preparatively satisfactory access is described to stable derivatives of D-actinospectose, a 4, 6-dideoxy-D-glycero-hexopyranos-2, 3-diulose (3a⇌ 3b) realized in spectinomycin (1) and a series of Calotropis cardenolides (2). Key steps are the conversions of the 6-deoxy-D-hydroxyglucal ester 8 either into the hexulose tribenzoate 10 (47%) by chlorination and hydrolysis, or into the α-ulosyl bromide 12 (76%) via NBS ...