2-Cyanotetrahydropyridine 9, bearing an indole-2-acetate moiety, was envisaged as a model synthetic equivalent of the dihydropyridinium cations A, which have been proposed as common biogenetic intermediates to both ngouniensine 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.
Biomimetic construction of the tetracyclic ring system of ngouniensine / D. Passarella, M. Martinelli, N. Llor, M. Amat, J. Bosch. - In: TETRAHEDRON. - ISSN 0040-4020. - 55:52(1999), pp. 14995-15000.
Biomimetic construction of the tetracyclic ring system of ngouniensine
D. Passarella;
1999
Abstract
2-Cyanotetrahydropyridine 9, bearing an indole-2-acetate moiety, was envisaged as a model synthetic equivalent of the dihydropyridinium cations A, which have been proposed as common biogenetic intermediates to both ngouniensine 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.
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