Synthesis of Analogs of GABA .15. Preparation and Resolution of Some Potent Cyclopentene and Cyclopentane Derivatives
- 1 January 1986
- journal article
- research article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 39 (6) , 855-864
- https://doi.org/10.1071/ch9860855
Abstract
A series of cyclopentene and cyclopentane analogues of GABA has been prepared utilizing a thermal cis -trans isomerization of the phthalimido β,γ -unsaturated acid (10) as the key step to obtain trans-4- aminocyclopent-2-ene-1-carboxylic acid (7). Resolution of some of the potent GABA analogues, in particular (+)-(4S)- and (-)-(4R)-4- aminocyclopent-1-ene-1-carboxylic acid (5), has been achieved by crystallization of isopropylideneribonolactone esters or pantolactone esters of the phthalimido -protected intermediates.Keywords
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