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Journal of Carbohydrate Chemistry Volume 21, 2002 - Issue 1-2
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Original Articles

A NEW APPROACH TO ISOLEVOGLUCOSENONE VIA THE 2,3-SIGMATROPIC REARRANGEMENT OF AN ALLYLIC SELENIDE

Zbigniew J. Witczak Department of Pharmaceutical Sciences, Nesbitt School of Pharmacy, Wilkes University, Wilkes-Barre, PA, 18766, U.S.A.Correspondence[email protected]
,
Peter Kaplon Department of Pharmaceutical Sciences, School of Pharmacy, University of Connecticut, 372 Fairfield Rd. U-92, Storrs, CT, 06269-2092, U.S.A.
&
Mark Kolodziej Department of Pharmaceutical Sciences, School of Pharmacy, University of Connecticut, 372 Fairfield Rd. U-92, Storrs, CT, 06269-2092, U.S.A.
Pages 143-148 | Received 16 Nov 2000, Accepted 31 Dec 2001, Published online: 28 Oct 2011
 
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Abstract

A convenient method is described for the synthesis of isolevoglucosenone 5, via allylic selenide 3, and its rearrangement to allylic alcohol 4, followed by oxidation with manganese oxide. Isolevoglucosenone 5, is produced in 62% overall yield.

ACKNOWLEDGMENTS

Financial support from the American Cancer Society, Institutional Grant to the University of Connecticut Health Center #ACSIN 152L-132 is gratefully acknowledged.

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