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Simple and Convenient Synthesis of Iboga-Functionalized Isoquinuclidines

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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.
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Keywords: 3-alkyl-5; 6-dihydropyridine; isoquinuclidine; lithium enolate

Document Type: Review Article

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

Publication date: 2004-04-01

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  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
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