New routes to isomerically pure cyclopentanes. Synthesis of (3S,4S)-3,4-bis(benzoyloxymethyl)cyclopentan-1-ol using palladium-catalyzed [2 + 3] cycloaddition

Article abstract of DOI:10.1055/s-1993-25815

Two different routes to the enantiomerically pure (3S,4S)-3,4-bis(benzoyloxymethyl)cyclopentan-1-ol (6), a useful intermediate for the synthesis of a number of natural products, are described. Formation of the chiral five-membered ring was achieved using a palladium-catalyzed [2 + 3] cycloaddition between 2-(acetoxymethyl)-3-(trimethylsilyl)propene and optically active methyl (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5- enofuranuronate or ethyl (4R,Z)-4,5-(isopropylidenedioxy)pent-2-enoate.