Total synthesis of (+)-korupensamine B via an atropselective intermolecular biaryl coupling

S Huang, TB Petersen, BH Lipshutz

Index: Huang, Shenlin; Petersen, Tue B.; Lipshutz, Bruce H. Journal of the American Chemical Society, 2010 , vol. 132, # 40 p. 14021 - 14023

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Citation Number: 39

Abstract

The asymmetric total synthesis of nonracemic korupensamine B is reported. It includes a newly designed and highly trans-diastereoselective (> 20: 1 dr) route to the tetrahydroisoquinoline ring and an unprecedented atropdiastereoselective Suzuki− Miyaura coupling for construction of the fully fashioned naphthylisoquinoline framework that invokes π stacking as a possible source of stereocontrol.