493039-10-4Relevant 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 (2007/10/03)
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.
An efficient procedure for the preparation of (1S,3R)- and (1S,3S)-1-amino-3-(hydroxymethyl)cyclopentanes
Rapoport, Henry,Chen, Yuewu,Mohareb, Rafat M.,Ahn, Jin Hee,Sim, Tae Bo,Ho, Jonathan Z.
, p. 1153 - 1156 (2007/10/03)
Enantiomerically pure (1S,3S)- and (1S,3R)-1-amino-3-(hydroxymethyl) cyclopentanes have been efficiently synthesized from L-aspartic acid. The title compounds are isosteres of ribose and may be used to construct nucleoside analogs with important antiviral
