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

Fingerprint

Cyclopentanes
Nucleosides
Ribose
Aspartic Acid
Antineoplastic Agents
Antiviral Agents

Keywords

  • Amino acid
  • Carbocycle
  • Enantioselectivity
  • Heterocycle
  • Nucleoside

ASJC Scopus subject areas

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

Cite this

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, Taebo; Ho, Jonathan Z.

In: Chemical and Pharmaceutical Bulletin, Vol. 51, No. 10, 01.10.2003, p. 1153-1156.

Research output: Contribution to journalArticle

Rapoport, Henry ; Chen, Yuewu ; Mohareb, Rafat M. ; Ahn, Jin Hee ; Sim, Taebo ; Ho, Jonathan Z. / An efficient procedure for the preparation of (1S,3R)- and (1S,3S)-1-amino-3-(hydroxymethyl)cyclopentanes. In: Chemical and Pharmaceutical Bulletin. 2003 ; Vol. 51, No. 10. pp. 1153-1156.
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