Total synthesis of (+)-korupensamine B via an atropselective intermolecular biaryl coupling.
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.
Huang
Shenlin
S
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA.
Petersen
Tue B
TB
Lipshutz
Bruce H
BH
D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D007546:Isoquinolines; D009281:Naphthalenes; C110657:korupensamine A