ISSN:
0947-6539
Keywords:
allylic substrates
;
amidinomycin
;
asymmetric syntheses
;
carbanucleosides
;
palladium catalysts
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.19950010812
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