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Synthetic transformations of higher terpenoids: XXII. Reactions of lambertianic acid derivatives with organozinc reagents obtained from ethyl bromoalkanoates

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Abstract

Reactions of 16-cyanomethyllambertianate with organozinc reagents obtained from ethyl esters of α-bromoacetic, α-bromopropionic, and α-bromobutyric acids gave the corresponding enaminoesters, β-ketoesters, and β-hydroxyesters of labdanoids whose yield depended on the reaction conditions and the structure of the α-bromoester. By Reformatsky reaction of 16-formylmethyllambertianate with α-bromoesters of carboxylic acids stereoisomeric β-hydroxyesters of labdanoids were synthesized.

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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. Shults, M. M. Shakirov, I. Yu. Bagryanskaya & G. A. Tolstikov

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  1. Yu. V. Kharitonov
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  2. E. E. Shults
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  3. M. M. Shakirov
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  4. I. Yu. Bagryanskaya
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  5. G. A. Tolstikov
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Correspondence to Yu. V. Kharitonov.

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Original Russian Text © Yu.V. Kharitonov, E.E. Shults, M.M. Shakirov, I.Yu. Bagryanskaya, G.A. Tolstikov, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 9, pp. 1340–1348.

For Communication XXI, see [1].

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Kharitonov, Y.V., Shults, E.E., Shakirov, M.M. et al. Synthetic transformations of higher terpenoids: XXII. Reactions of lambertianic acid derivatives with organozinc reagents obtained from ethyl bromoalkanoates. Russ J Org Chem 46, 1339–1347 (2010). https://doi.org/10.1134/S1070428010090137

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  • DOI: https://doi.org/10.1134/S1070428010090137

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