20-ISO-20-Deethylaspidospermidine
- 1 January 1972
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 2 (5) , 285-290
- https://doi.org/10.1080/00397917208061982
Abstract
The two-step process of hydrogenation of l-alkyl-3-acylpyridinium salts and cyclization of the resultant 1, 4, 5, 6-tetrahydropyridines has been the foundation of a general scheme of alkaloid synthesis.1 Its application in the indole alkaloid field has yielded ready access to tetrahydro-β-carboline systems, e.g. 1a → 2 → eburnamonine.2 Since acid treatment of Nb -acyl derivatives of substances related to la has been shown to lead to products of indole β-cyclization3, it became of interest to test the cyclization behavior of the vinylogous imide lb, prepared by the dicyclohexylcarbodiimide-induced acylation of 3-acetyl-1, 4, 5, 6-tetrahydropyridine4 with indoleacetic acid. Treatment of lb with boron trifluoride gave a 62 yield of ketolactam 3a. Thus a two-step entry into the pentacyclic Aspidosperma alkaloid skeleton is on hand.Keywords
This publication has 5 references indexed in Scilit:
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- General Methods of Synthesis of Indole Alkaloids. IV. A Synthesis of dl-Eburnamonine1,2Journal of the American Chemical Society, 1965
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