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Cyclocondensation of methyl 12-aminodehydroabietate with aldehydes and cyclopentadiene. Synthesis of tricyclic diterpenoide fused to tetrahydroquinoline

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Abstract

Three-component cyclocondensation of methyl 12-aminodehydroabietate with cyclopentadiene and formaldehyde or acetaldehyde under acid catalysis afforded polysubstituted naphthoquinoline derivatives with fused oxetanocyclopentane and cyclopentene fragments. Ozonation of the double bond in the N-trifluoroacetyl cyclopentene derivatives gave the corresponding ozonide.

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, Ufa, 450075, Bashkortostan, Russia

    A. G. Tolstikov, R. G. Savchenko, E. S. Lukina, D. V. Nedopekin, R. M. Shakirova & V. N. Odinokov

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  1. A. G. Tolstikov
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  2. R. G. Savchenko
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  3. E. S. Lukina
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  4. D. V. Nedopekin
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  5. R. M. Shakirova
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  6. V. N. Odinokov
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Corresponding author

Correspondence to V. N. Odinokov.

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Original Russian Text © A.G. Tolstikov, R.G. Savchenko, E.S. Lukina, D.V. Nedopekin, R.M. Shakirova, V.N. Odinokov, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 1, pp. 136–140.

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Tolstikov, A.G., Savchenko, R.G., Lukina, E.S. et al. Cyclocondensation of methyl 12-aminodehydroabietate with aldehydes and cyclopentadiene. Synthesis of tricyclic diterpenoide fused to tetrahydroquinoline. Russ J Org Chem 50, 128–132 (2014). https://doi.org/10.1134/S1070428014010230

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  • DOI: https://doi.org/10.1134/S1070428014010230

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