New strategy for the synthesis of tetrahydroisoquinoline alkaloids

Philip Magnus; Kenneth S Matthews; Vince Lynch

doi:10.1021/ol034683+

New strategy for the synthesis of tetrahydroisoquinoline alkaloids

Org Lett. 2003 Jun 12;5(12):2181-4. doi: 10.1021/ol034683+.

Authors

Philip Magnus¹, Kenneth S Matthews, Vince Lynch

Affiliation

¹ Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA. p.magnus@mail.utexas.edu

PMID: 12790559
DOI: 10.1021/ol034683+

Abstract

[reaction: see text] A general strategy for the formation of 1,3-cis-substituted tetrahydroisoquinolines is described from ortho-iodo imines involving Larock isoquinoline synthesis, addition of organolithium compounds to unactivated isoquinolines, and ionic hydrogenation. In addition, a new synthesis of lactams via an unprecedented azide cyclization in the presence of a sulfonium ion is described.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Hydrogenation
Imines / chemistry
Isoquinolines / chemical synthesis*
Isoquinolines / chemistry
Stereoisomerism

Substances

Alkaloids
Imines
Isoquinolines
isoquinoline

Grants and funding

GM32718/GM/NIGMS NIH HHS/United States