The Journal of Organic Chemistry

Stereocontrolled Synthesis of ent-Grindelic Acid. A Useful Example of Diastereofacial Guidance in an Oxonium Ion-Initiated Pinacolic Ring Expansion

LA Paquette, HL Wang

Index: Paquette, Leo A.; Dullweber, Uta; Branan, Bruce M. Heterocycles, 1994 , vol. 37, # 1 p. 187 - 192

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Citation Number: 38

Abstract

An enantioselective synthesis of (+)-grindelic acid is described, confirming that the dextrorotatory enantiomer is antipodal to the natural diterpenoid. The optically pure bicyclic ketone 5 representing the AB ring system is constructed from the levorotatory Wieland-