493039-01-3Relevant academic research and scientific papers
Enantiospecific synthesis of carbapentostatins
Ho, Jonathan Z.,Mohareb, Rafat M.,Ahn, Jin Hee,Sim, Tae Bo,Rapoport, Henry
, p. 109 - 114 (2003)
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 γ-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.
