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Synthesis of 8,9-(1,3-benzodioxolo-5,6)-5-azatricyclo[8.2.1.01,5]tridec-11-en-6-one. A convenient route to structural analogs of the alkaloid cephalotaxine

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Abstract

A synthetic route to 8,9-(1,3-benzodioxolo-5,6)-5-azatricyclo[8.2.1.01,5]tridec-11-en-6-one structurally isomeric to the pentacyclic cephalotaxine nucleus is suggested. The route is based on the sequence including diallylboration of 2-pyrrolidinone and intramolecular metathesis of the resulting 2,2-diallylpyrrolidine, giving rise to 1-azaspiro[4.4]non-7-ene. This product was N-acylated with 6-bromohomopiperonylic acid chloride and then subjected to intramolecular cyclization according to the Heck reaction.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    N. Yu. Kuznetsov, I. V. Zhun’, V. N. Khrustalev & Yu. N. Bubnov

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  1. N. Yu. Kuznetsov
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  2. I. V. Zhun’
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  3. V. N. Khrustalev
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  4. Yu. N. Bubnov
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Dedicated to Academicians A. L. Buchachenko and N. S. Zefirov on the occasion of their 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2160–2163, September, 2005.

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Kuznetsov, N.Y., Zhun’, I.V., Khrustalev, V.N. et al. Synthesis of 8,9-(1,3-benzodioxolo-5,6)-5-azatricyclo[8.2.1.01,5]tridec-11-en-6-one. A convenient route to structural analogs of the alkaloid cephalotaxine. Russ Chem Bull 54, 2229–2232 (2005). https://doi.org/10.1007/s11172-006-0103-8

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  • DOI: https://doi.org/10.1007/s11172-006-0103-8

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