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.

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

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

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ACKNOWLEDGMENTS

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