AN ENANTIOSELECTIVE SYNTHESIS OF THE STRYCHNOS ALKALOID (-)-TUBIFOLINE

Authors
AMAT M COLL MD PASSARELLA D BOSCH J
Citation
M. Amat et al., AN ENANTIOSELECTIVE SYNTHESIS OF THE STRYCHNOS ALKALOID (-)-TUBIFOLINE, Tetrahedron : asymmetry, 7(10), 1996, pp. 2775-2778
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
10
Year of publication
1996
Pages
2775 - 2778
Database
ISI
SICI code
0957-4166(1996)7:10<2775:AESOTS>2.0.ZU;2-G
Abstract
An enantioselective synthesis of the Strychnos alkaloid (-)-tubifoline , involving the kinetic resolution of racemic 1-(3-pyridyl)ethanol, th e orthoester Claisen rearrangement of the enantiopure allylic alcohol 5, Smith indolization of the resulting 4-piperidineacetate 6, photocyc lization of chloroacetamide 9, and final transannular cyclization, is reported. Copyright (C) 1996 Elsevier Science Ltd