Simple and Convenient Synthesis of Iboga-Functionalized Isoquinuclidines

Author(s): A. A. Maia, R. P. Freitas-Gil, L. F. Gil, C. Marazano.

Journal Name: Letters in Organic Chemistry

Volume 1 , Issue 2 , 2004

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Synthesis of Iboga-functionalized isoquinuclidine ring system and alkylated derivatives from commercially available 3-ethyl-pyridine, is reported. The key-step for isoquinuclidine synthesis is a cycloaddition between methyl acrylate and N-benzyl-3- ethyl-5,6-dihydropyridine obtained in situ from N-benzyl-3-ethyl-4-methoxy-1,4,5,6- tetrahydropyridine. Further treatment of isoquinuclidine lithium enolate with appropriate electrophiles gave alkylated products with good stereoselectivity.

Keywords: 3-alkyl-5, 6-dihydropyridine, isoquinuclidine, lithium enolate

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Article Details

Year: 2004
Page: [168 - 170]
Pages: 3
DOI: 10.2174/1570178043488446
Price: $65

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