ENANTIOSELECTIVE SYNTHESIS OF THE TRANS-2,6-DIALKYLPIPERIDINE ALKALOIDS (2R,6R)-LUPETIDINE AND (2R,6R)-SOLENOPSIN-A

Authors
AMAT M HIDALGO J LLOR N BOSCH J
Citation
M. Amat et al., ENANTIOSELECTIVE SYNTHESIS OF THE TRANS-2,6-DIALKYLPIPERIDINE ALKALOIDS (2R,6R)-LUPETIDINE AND (2R,6R)-SOLENOPSIN-A, Tetrahedron : asymmetry, 9(14), 1998, pp. 2419-2422
Citations number
63
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
14
Year of publication
1998
Pages
2419 - 2422
Database
ISI
SICI code
0957-4166(1998)9:14<2419:ESOTTA>2.0.ZU;2-E
Abstract
The enantioselective synthesis of the trans-2,6-dialkylpiperidine alka loids (2R,6R)-lupetidine and (2R,6R)solenopsin A from 6-methyl-2-piper idone 1 is described. The key step of this synthesis consists of the a ddition of a dialkylcopper derivative to the thioimidate salt 3 follow ed by sodium borohydride reduction of the resulting iminium salt. (C) 1998 Elsevier Science Ltd. All rights reserved.