A Facile Synthesis of (−)-(4R,5R)-4,5-(Isopropylidenedioxy)-2-cyclopentenone, a Useful Precursor to d-Like Carbanucleosides

Abstract

A facile synthesis of (−)-(4R,5R)-4,5-(isopropylidenedioxy)-2-cyclopentenone ((−)-2), as a precursor to d-like carbanucleosides, is described in 5 steps from (1S,4R)-4-acetoxycyclopent-2-en-1-ol (3). Compound 3 has also been described in the literature as amenable to the formation of (+)-2, thus making both the d-like and l-like carbanucleosides available from the same readily available 3.

Acknowledgment

This research was supported by funds from the Department of Health and Human Services (AI48495), which is appreciated.