An efficient procedure for the preparation of (1S,3R)- and (1S,3S)-1-amino-3-(hydroxymethyl)cyclopentanes

Henry Rapoport, Yuewu Chen, Rafat M. Mohareb, Jin Hee Ahn, Taebo Sim, Jonathan Z. Ho

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

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 and antineoplastic activities as demonstrated by a concise total synthesis of (+)-4′-deoxycarbapentostatin nucleoside.

Original languageEnglish
Pages (from-to)1153-1156
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume51
Issue number10
DOIs
Publication statusPublished - 2003 Oct 1
Externally publishedYes

Keywords

  • Amino acid
  • Carbocycle
  • Enantioselectivity
  • Heterocycle
  • Nucleoside

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Pharmacology

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