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Synthetic transformations of higher terpenoids: XIV. Heterocyclization reactions of 15,16,18-ricarboxylabdadiene. New nitrogen-containing diterpenoids

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Abstract

The oxidation of methyl lambertianate with Jones’ reagent formed the corresponding anhydride which reacted with amines to form N-substituted terpenoid maleimides. New maleimides demonstrated high activity and stereoselectivity in the Diels-Alder reaction with cyclopentadiene. The condensation of the diterpenoid anhydride with hydrazines led to the formation of derivatives of 3,6-dioxo-1,2,3,6-tetrahydropyridazines of labdane type.

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, 630090, Russia

    Yu. V. Kharitonov, E. E. Shul’ts, M. M. Shakirov & G. A. Tolstikov

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  1. Yu. V. Kharitonov
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  2. E. E. Shul’ts
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  3. M. M. Shakirov
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  4. G. A. Tolstikov
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Additional information

Original Russian Text © Yu.V. Kharitonov, E.E. Shul’ts, M.M. Shakirov, G.A. Tolstikov, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 5, pp. 725–735.

For Communication XIII see [1].

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Kharitonov, Y.V., Shul’ts, E.E., Shakirov, M.M. et al. Synthetic transformations of higher terpenoids: XIV. Heterocyclization reactions of 15,16,18-ricarboxylabdadiene. New nitrogen-containing diterpenoids. Russ J Org Chem 42, 707–718 (2006). https://doi.org/10.1134/S1070428006050113

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  • DOI: https://doi.org/10.1134/S1070428006050113

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