Diastereoselective synthesis of (+/-)-(3-aminocyclopentane)alkylphosphinic acids, conformationally restricted analogues of GABA

Jane R Hanrahan; Kenneth N Mewett; Mary Chebib; Susana Matos; Con T Eliopoulos; Colm Crean; Rohan J Kumar; Peter Burden; Graham A R Johnston

doi:10.1039/b604002k

Diastereoselective synthesis of (+/-)-(3-aminocyclopentane)alkylphosphinic acids, conformationally restricted analogues of GABA

Org Biomol Chem. 2006 Jul 7;4(13):2642-9. doi: 10.1039/b604002k. Epub 2006 Jun 1.

Authors

Jane R Hanrahan¹, Kenneth N Mewett, Mary Chebib, Susana Matos, Con T Eliopoulos, Colm Crean, Rohan J Kumar, Peter Burden, Graham A R Johnston

Affiliation

¹ The Faculty of Pharmacy, University of Sydney, NSW, Australia. janeh@pharm.usyd.edu.au

PMID: 16791329
DOI: 10.1039/b604002k

Abstract

A divergent synthesis of both diastereoisomers of (+/-)-(3-aminocyclopentane)alkylphosphinic acid is described. Both diastereoisomers are obtained in 5 steps from the key (+/-)-(3-hydroxycyclopent-1-ene)alkylphosphinate esters which are prepared via a palladium catalysed C-P bond forming reaction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Magnetic Resonance Spectroscopy
Phosphinic Acids / chemical synthesis*
Phosphinic Acids / chemistry
Spectrometry, Mass, Electrospray Ionization
Stereoisomerism
gamma-Aminobutyric Acid / analogs & derivatives*

Substances

Phosphinic Acids
gamma-Aminobutyric Acid