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

Shenlin Huang; Tue B Petersen; Bruce H Lipshutz

doi:10.1021/ja1065202

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

J Am Chem Soc. 2010 Oct 13;132(40):14021-3. doi: 10.1021/ja1065202.

Authors

Shenlin Huang¹, Tue B Petersen, Bruce H Lipshutz

Affiliation

¹ Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA.

PMID: 20849111
DOI: 10.1021/ja1065202

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.

MeSH terms

Isoquinolines / chemical synthesis*
Isoquinolines / chemistry
Naphthalenes / chemical synthesis*
Naphthalenes / chemistry
Stereoisomerism

Substances

Isoquinolines
Naphthalenes
korupensamine A