Simple and Convenient Synthesis of Iboga-Functionalized Isoquinuclidines

A.   A.   Maia; R.   P.   Freitas-Gil; L.   F.   Gil; C.      Marazano

doi:10.2174/1570178043488446

Abstract

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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Letters in Organic Chemistry

Title: Simple and Convenient Synthesis of Iboga-Functionalized Isoquinuclidines

Volume: 1 Issue: 2

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

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

Abstract: 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.

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Maia A. A., Freitas-Gil P. R., Gil F. L. and Marazano C., Simple and Convenient Synthesis of Iboga-Functionalized Isoquinuclidines, Letters in Organic Chemistry 2004; 1 (2) . https://dx.doi.org/10.2174/1570178043488446