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Simple and Convenient Synthesis of Iboga-Functionalized Isoquinuclidines

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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

Document Type: Review Article

DOI: https://doi.org/10.2174/1570178043488446

Affiliations: Universidade Federal de Minas Gerais, Departamento de Quimica, Belo Horizonte, 31270-901, Brazil.

Publication date: 2004-04-01

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