Convenient route to both enantiomers of a highly functionalized trans-disubstituted cyclopentene. Synthesis of the carbocyclic core of the nucleoside BCA

Abstract

Synthesis of both enantiomers of a highly functionalized cyclopentenol derivative, versatile building block for a vast array of biologically active compounds, is described. The key steps involve stereocontrolled synthesis of a diene with two syn-disposed substituents from a (R)-(+)-glyceraldehyde derivative, ring-closing metathesis of this diene, and functional group manipulation of the resulting trans-disubstituted cyclopentene. One of the enantiomers of the cyclopentenol thus obtained has been converted to an amino cyclopentene, the carbocyclic core of the nucleoside (-)-BCA, a potent inhibitor of HIV reverse transcriptase.