Enantiospecific synthesis of carbapentostatins |
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Authors: | Ho Jonathan Z Mohareb Rafat M Ahn Jin Hee Sim Tae Bo Rapoport Henry |
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Institution: | Department of Chemistry, University of California, Berkeley, California 94720, USA. jonathan_ho@merck.com |
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Abstract: | In this paper we describe enantioselective syntheses of (+)-carbapentostatin (8) and its cyclopentyl analogue 12b. A new and efficient one-pot, two-step preparation of aldehyde 15 has been developed, based on the borane reduction of N-Pf-protected L-aspartic acid gamma-methyl ester (13) and Swern oxidation of the resulting alcohol. Homologation to diester 18 and ring formation by Dieckman cyclization, followed by reduction and dehydration steps, afford the 4-amino-1-cyclopentenemethanol derivative 22. Hydroboration and oxidation transform this compound stereospecifically into aminocyclopentanol 26, the key aminocyclitol component for an asymmetric synthesis of (+)-carbapentostatin. |
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