AN ENANTIOSELECTIVE SYNTHESIS OF T-BUTOXYCARBAMOYL-1-METHOXYCARBONYL-2-CYCLOPENTENE - A USEFUL, GENERAL BUILDING-BLOCK

The amino acid derivative in the title represents an important buildin g block for the synthesis of a number of biologically important target s such as the antiviral carbanucleosides and amidinomycin. By using as ymmetric palladium-catalyzed desymmetrization of meso-2-ene-1,4-diols, cis-1,4-dibenzoyloxy-2-cyclopentene can be converted to the enantiome rically pure title compound in only four steps. Chemoselective ester r eduction allows entry into the domain of carbanucleosides, whereas dou ble-bond reduction provides the precursor for amidinomycin. In an anci llary study, a facile diastereoselective cis-hydroxylation provides am inocyclopentitols, compounds that have proven to be potent glycosidase inhibitors.