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Synthesis and transformations of 2,4-dioxa- and 2,4-diazaspiro[5.5]undecanones equipped with a diterpenoid substituent

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Abstract

The Diels—Alder reaction of 16-(3-trimethylsilyloxybutadienyl)furanolabdanoids with 5-methylene(arylidene)-3,3-dimethyl-2,4-dioxane-1,5-diones or 5-methylene(arylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-triones in the presence of l-proline proceeded regioselectively and led to 7-furanoterpenyl-substituted 3,3-dimethyl-2,4-dioxaspiro[5.5]-undecane-1,5,9-triones or 2,4-dimethyl-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraones, respectively. The conditions for the one-pot synthesis of terpenyl-substituted dioxaspiro-[5.5]undecane-1,5,9-triones by the l-proline catalyzed three-component Knoevenagel—Diels—Alder reaction of diterpenoid enone, aldehyde, and the Meldrum’s acid were proposed. A diterpenoid analog of anticancer agents with an 11-(biphenyl-4-yl)-2,4-di-oxaspiro[5.5]undecanone substituent was synthesized by the Suzuki reaction of the obtained bromophenyl-substituted spirocyclic ketone with 3,4,5-(trimethoxyphenyl)boronic acid.

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Acknowledgements

The authors express their gratitude to the Chemical Service Center for Collective Use of the Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences for the spectral and analytical studies.

Funding

This work was financially supported by the Russian Science Foundation (Project No. 23-73-00077).

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    M. E. Mironov & E. E. Shults

  2. Novosibirsk State University, 1 ul. Pirogova, 630090, Novosibirsk, Russian Federation

    M. E. Mironov

Authors
  1. M. E. Mironov
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  2. E. E. Shults
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Correspondence to E. E. Shults.

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The authors declare no competing interests.

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Dedicated to the memory of Academician of the Russian Academy of Sciences G. A. Tolstikov (1933–2013).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 10, pp. 2453–2465, October, 2023.

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Mironov, M.E., Shults, E.E. Synthesis and transformations of 2,4-dioxa- and 2,4-diazaspiro[5.5]undecanones equipped with a diterpenoid substituent. Russ Chem Bull 72, 2453–2465 (2023). https://doi.org/10.1007/s11172-023-4047-z

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  • DOI: https://doi.org/10.1007/s11172-023-4047-z

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