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; Tae Bo Sim; Jonathan Z. Ho

doi:10.1248/cpb.51.1153

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, Tae Bo Sim, Jonathan Z. Ho

Research output: Contribution to journal › Article › peer-review

4 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 language	English
Pages (from-to)	1153-1156
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	51
Issue number	10
DOIs	https://doi.org/10.1248/cpb.51.1153
Publication status	Published - 2003 Oct

Keywords

Amino acid
Carbocycle
Enantioselectivity
Heterocycle
Nucleoside

ASJC Scopus subject areas

General Chemistry
Drug Discovery

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10.1248/cpb.51.1153

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keywords = "Amino acid, Carbocycle, Enantioselectivity, Heterocycle, Nucleoside",

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AU - Rapoport, Henry

AU - Chen, Yuewu

AU - Mohareb, Rafat M.

AU - Ahn, Jin Hee

AU - Sim, Tae Bo

AU - Ho, Jonathan Z.

PY - 2003/10

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AB - 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.

KW - Amino acid

KW - Carbocycle

KW - Enantioselectivity

KW - Heterocycle

KW - Nucleoside

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JO - Chemical and Pharmaceutical Bulletin

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IS - 10

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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