Biomimetic construction of the tetracyclic ring system of ngouniensine

Authors
Passarella, D Martinelli, M Llor, N Amat, M Bosch, J
Citation
D. Passarella et al., Biomimetic construction of the tetracyclic ring system of ngouniensine, TETRAHEDRON, 55(52), 1999, pp. 14995-15000
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
52
Year of publication
1999
Pages
14995 - 15000
Database
ISI
SICI code
0040-4020(199912)55:52<14995:BCOTTR>2.0.ZU;2-5
Abstract
2-Cyanotetrahydropyridine 9, bearing an indole-2-acetate moiety, was envisa ged as a model synthetic equivalent of the dihydropyridinium cations A, whi ch have been proposed as common biogenetic intermediates to both ngouniensi ne and Strychnos indole alkaloids. Lewis acid-promoted cyclization of the O -silyl ketene acetal derived from 9 led to the ngouniensine-type derivative 11. (C) 1999 Elsevier Science Ltd. All rights reserved.