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Synthetic transformations of sesquiterpene lactones 6. Alantolactone and isoalantolactone derivatives in the Heck reaction

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Abstract

The Heck reaction of the eudesman-type methylidenelactones (alantolactone, alloalantolactone, and 4,15-epoxyisoalantolactone) with haloarenes afforded the corresponding (E)-13-aryleudesma-4(15),11(13)-dien-8β,12-olides and 11-arylmethyl-13-noreudesma-4(15),7(11)-dien-8α,12-olides. The yields and the ratios of the arylation products depended on the reaction conditions and the structure of lactone. Certain side processes were found to take place.

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

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

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  1. E. E. Shul’ts
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  2. A. V. Belovodskii
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  3. M. M. Shakirov
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  4. G. A. Tolstikov
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Correspondence to E. E. Shul’ts.

Additional information

For Part 5, see Ref. 1.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1959–1968, October, 2012.

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Shul’ts, E.E., Belovodskii, A.V., Shakirov, M.M. et al. Synthetic transformations of sesquiterpene lactones 6. Alantolactone and isoalantolactone derivatives in the Heck reaction. Russ Chem Bull 61, 1975–1985 (2012). https://doi.org/10.1007/s11172-012-0274-4

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  • DOI: https://doi.org/10.1007/s11172-012-0274-4

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