157555-70-9Relevant articles and documents
An Enantioselective Synthesis of cis-4-tert-Butoxycarbamoyl-1-methoxycarbonyl-2-cyclopentene - A Useful, General Building Block
Trost, Barry M.,Stenkamp, Dirk,Pulley, Shon R.
, p. 568 - 572 (2007/10/03)
The amino acid derivative in the title represents an important building block for the synthesis of a number of biologically important targets such as the antiviral carbanucleosides and amidinomycin.By using asymmetric palladium-catalyzed desymmetrization of meso-2-ene-1,4-diols, cis-1,4-dibenzoyloxy-2-cyclopentene can be converted to the enantiomerically pure title compound in only four steps.Chemoselective ester reduction allows entry into the domain of carbanucleosides, whereas double-bond reduction provides the precursor for amidinomycin.In an ancillary study, a facile diastereoselective cis-hydroxylation provides aminocyclopentitols, compounds that have proven to be potent glycosidase inhibitors. - Keywords: allylic substrates; amidinomycin; asymmetric syntheses; carbanucleosides; palladium catalysts
