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Synthetic transformations of methylenelactones of eudesmanic type. Behavior of isoalantolactone under the conitions of heck reaction

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Abstract

By Heck reaction of isoalantolactone with aryl bromides or aryl iodides (3aR,4aS, 8aR,9aR,E)-3-arylmethylidene-8a-methyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-ones and (4aS,8aR,9aS)-3-arylmethyl-8a-methyl-5-methylidene-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-ones, products of the double bond shift, were synthesized. The yields of the arylation products depend on the nature of the catalytic system and on the structure of the aryl halide. The structures of (3aR,4aS,8aR,9aR,E)-3-(3,4-dimethoxybenzylidene)-8amethyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-one and (4aS,8aR,9aS)-3-(2-methylsulfanylbenzyl)-8amethyl-5-methylidene-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-one were proved by XRD analysis.

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Authors and Affiliations

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

    A. V. Belovodskii, E. E. Shults, M. M. Shakirov, I. Yu. Bagryanskaya, Yu. V. Gatilov & G. A. Tolstikov

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  1. A. V. Belovodskii
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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. Yu. V. Gatilov
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  6. G. A. Tolstikov
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Corresponding author

Correspondence to E. E. Shults.

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Original Russian Text © A.V. Belovodskii, E.E. Shults, M. M. Shakirov, I.Yu. Bagryanskaya, Yu.V. Gatilov, G.A. Tolstikov, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 11, pp. 1710–1724.

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Belovodskii, A.V., Shults, E.E., Shakirov, M.M. et al. Synthetic transformations of methylenelactones of eudesmanic type. Behavior of isoalantolactone under the conitions of heck reaction. Russ J Org Chem 46, 1719–1734 (2010). https://doi.org/10.1134/S1070428010110199

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  • DOI: https://doi.org/10.1134/S1070428010110199

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