Enantiospecific synthesis of carbapentostatins

Jonathan Z. Ho, Rafat M. Mohareb, Jin Hee Ahn, Tae Bo Sim, Henry Rapoport

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)

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 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.

Original languageEnglish
Pages (from-to)109-114
Number of pages6
JournalJournal of Organic Chemistry
Volume68
Issue number1
DOIs
Publication statusPublished - 2003 Jan 10
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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