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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 10
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Original Articles

SYNTHESIS OF BETULIN DERIVATIVES WITH SOLID SUPPORTED REAGENTS

Serge Lavoie Université du Québec à Chicoutimi, LASEVE, 555 boul. Université, Chicoutimi, Queébec, G7H 2B1, Canada
,
André Pichette Université du Québec à Chicoutimi, LASEVE, 555 boul. Université, Chicoutimi, Queébec, G7H 2B1, Canada
,
François-Xavier Garneau Université du Québec à Chicoutimi, LASEVE, 555 boul. Université, Chicoutimi, Queébec, G7H 2B1, Canada
,
Michel Girard Sir F. G. Banting Research Center, Bureau of Biologics and Radiopharmaceuticals, Therapeutic Products Program, Health Canada, Tunney's Pasture, Ottawa, Ontario, K1A 0L2, Canada
&
Daniel Gaudet Chicoutimi Hospital Research Unit, 305 St-Vallier, Chicoutimi, Québec, G7H 5H6, Canada
Pages 1565-1571 | Received 03 Aug 2000, Published online: 02 Aug 2010
 
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Abstract

Betulin–allobetulin transformation is effected with ferric nitrate or ferric chloride adsorbed onto silica gel or alumina, in excellent yields. In addition, allobetulin can be converted to allobetulone with silica adsorbed ferric nitrate or to 19β,28- epoxy-A-neo-18α-olean-3(5)-ene and 19β,28-epoxy-A-neo-5β-methyl-25-nor-18α-olean-9-ene with silica or alumina adsorbed ferric chloride.

ACKNOWLEDGMENTS

We thank Jimmy Bouchard, Bruce Black, and Brian Dawson for their assistance in the NMR experiments. The financial support of the Fondation de l'UQAC is gratefully acknowledged. SL thanks PAIR, Bourse Paul-Émile-Boulet, and Association des diplômé (e)s et ami(e)s de I'UQAC for graduate scholarships.

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