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Synthetic transformations of sesquiterpene lactones 9.* Synthesis of 13-(pyridinyl)eudesmanolides

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of isoalantolactone, a sesquiterpene α-methylidene-γ-lactone, with bromo(iodo)pyridines under the Heck reaction conditions gave 3-(pyridylmethylidene)-8а-methyldecahydronaphtho[2,3-b]furan-2(3Н)-ones and 3-(pyridylmethyl)-8а-methyloctahydronaphtho[2,3-b]-furan-2(4Н)-ones, products of double bond migration. The yield and product ratio depended on the reaction conditions and the nature of halopyridine. The effectiveness of Pd(OAc)2–caffeine catalytic system was demonstrated in this reaction.

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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 Akademika Lavrentieva Ave., Novosibirsk, 630090, Russia

    Sergey S. Patrushev, Makhmut M. Shakirov & Elvira E. Shults

  2. Novosibirsk State University, Pirogova St., Novosibirsk, 630090, Russia

    Sergey S. Patrushev & Elvira E. Shults

Authors
  1. Sergey S. Patrushev
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  2. Makhmut M. Shakirov
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  3. Elvira E. Shults
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Correspondence to Elvira E. Shults.

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* For Communication 8, see1.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(3), 165–171

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Patrushev, S.S., Shakirov, M.M. & Shults, E.E. Synthetic transformations of sesquiterpene lactones 9.* Synthesis of 13-(pyridinyl)eudesmanolides. Chem Heterocycl Comp 52, 165–171 (2016). https://doi.org/10.1007/s10593-016-1855-1

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