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Convenient Route to Both Enantiomers of a Highly Functionalized Trans-Disubstituted Cyclopentene. Synthesis of the Carbocyclic Core of the Nucleoside BCA

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journal contribution
posted on 13.05.2005, 00:00 by Shyamapada Banerjee, Sarita Ghosh, Saikat Sinha, Subrata Ghosh
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.