Successful Asymmetric Diels-Alder Approach To Optically Active C-Nucleosides. Enantioselective Total Synthesis of D-Showdomycin and D-2,5-Anhydroallose Derivatives

Abstract

Using an asymmetric Diels-Alder reaction of (S)S-3-(2-pyridylsulfinyl)acrylate with furan, a highly enantioselective synthesis of a common key intermediate (+)-(1) was achieved, and this was successfully converted to C-nucleosides, D-showdomycin (2) and D-3,4-0-isopropylidene-2,5-anhydroallose (3). © 1987, The Pharmaceutical Society of Japan. All rights reserved.