Enantioselective modification of the Pomeranz-Fritsch-Bobbitt synthesis oftetrahydroisoquinoline alkaloids: synthesis of (-)-salsolidine and (-)-carnegine

Authors
Gluszynska, A Rozwadowska, MD
Citation
A. Gluszynska et Md. Rozwadowska, Enantioselective modification of the Pomeranz-Fritsch-Bobbitt synthesis oftetrahydroisoquinoline alkaloids: synthesis of (-)-salsolidine and (-)-carnegine, TETRAHEDR-A, 11(11), 2000, pp. 2359-2366
Citations number
29
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
11
Year of publication
2000
Pages
2359 - 2366
Database
ISI
SICI code
0957-4166(20000616)11:11<2359:EMOTPS>2.0.ZU;2-0
Abstract
(-)-Salsolidine 7 and (-)-carnegine 8 were prepared in 46 and 36% e.e., res pectively, by enantioselective addition of methyllithium to the Pomeranz-Fr itsch imine 13 in the presence of ligands 9 12, followed by acid-catalyzed cyclization and hydrogenolysis. (C) 2000 Elsevier Science Ltd, All rights r eserved.