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Synthesis of 4,6-Diarylbicyclo[3.3.1]nona-3,6-dien-2-ones

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Abstract

Bicyclo[3.3.1]nonane system is an important structural motif in many natural compounds. This article describes a short synthetic route to the bicyclo[3.3.1]nonane system via aldol condensation. The proposed strategy is based on the use of cyclohex-2-en-1-ones containing an additional carbonyl group in the side chain as a key precursor. The approach showed good results for compounds with electron-donating groups in aromatic substituents. An obvious advantage of such synthesis of bicyclo[3.3.1]nona-3,6-dien-2-ones is that it involves two steps and requires only two building blocks, namely a Mannich base and ethyl acetoacetate.

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Authors and Affiliations

  1. Belarusian State Technological University, 220006, Minsk, Belarus

    S. G. Mikhalyonok, V. S. Bezborodov, N. M. Kuz’menok, A. I. Savelyeu & A. S. Arol

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  1. S. G. Mikhalyonok
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  2. V. S. Bezborodov
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  3. N. M. Kuz’menok
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  4. A. I. Savelyeu
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  5. A. S. Arol
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Correspondence to A. S. Arol.

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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 7, pp. 935–945 https://doi.org/10.31857/S0514749223070078.

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Mikhalyonok, S.G., Bezborodov, V.S., Kuz’menok, N.M. et al. Synthesis of 4,6-Diarylbicyclo[3.3.1]nona-3,6-dien-2-ones. Russ J Org Chem 59, 1171–1179 (2023). https://doi.org/10.1134/S1070428023070072

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