Abstract
Reactions of methyl phlomisoate with methyl acrylate, phenyl acrylate, methyl vinyl ketone, phenyl vinyl ketone, or N-substituted acrylamides catalyzed by Pd(OAc)2 in the presence of Cu(OAc)2, p-benzoquinone in the mixture of propionic acid and acetonitrile proceed regio- and stereoselectively with the formation of (E)-16-vinyl labdatrienoates. The oxidative coupling under these conditions of the methyl phlomisoate with styrene results in a mixture of 15,16-distyryl-, 16-styryl-, and 16-(1-phenylvinyl)-derivatives of furanolabdanoid.
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Original English Text © Yu.V. Kharitonov, O.I. Kremenko, E.E. Shults, M.M. Shakirov, G.A. Tolstikov, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 11, pp. 1707–1718.
For Communication XXXI, see [1].
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Kharitonov, Y.V., Kremenko, O.I., Shults, E.E. et al. Synthetic transformations of higher terpenoids: XXXII. Synthesis of 16-alkenyl-substituted labdatrienes by oxidative coupling of methyl phlomisoate with alkenes. Russ J Org Chem 49, 1690–1702 (2013). https://doi.org/10.1134/S1070428013110225
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DOI: https://doi.org/10.1134/S1070428013110225