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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 9
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Original Articles

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

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Pages 1477-1481 | Received 31 Jul 2002, Published online: 16 Aug 2006
 

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.

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