Tetrahedron

Enantioselective syntheses of tremulenediol A and tremulenolide A

BL Ashfeld, SF Martin

Index: Ashfeld, Brandon L.; Martin, Stephen F. Tetrahedron, 2006 , vol. 62, # 45 p. 10497 - 10506

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Citation Number: 34

Abstract

A concise entry to the skeleton of the tremulane sesquiterpenes is described that culminated in the first enantioselective syntheses of tremulenediol A and tremulenolide A. The approach features a series of efficient transition metal-catalyzed reactions commencing with an enantioselective rhodium (II)-catalyzed intramolecular cyclopropanation followed by a regioselective allylic alkylation and a diastereoselective rhodium (I)-catalyzed [5+ 2] ...