New strategy for the synthesis of tetrahydroisoquinoline alkaloids.
[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.
Magnus
Philip
P
Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA. p.magnus@mail.utexas.edu
Matthews
Kenneth S
KS
Lynch
Vince
V
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D007097:Imines / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D007097:Imines; D007546:Isoquinolines; C039109:isoquinoline