Abstract: The reaction of phlomisoic acid methyl ester with styrene, catalyzed by Pd(OAc)(2), in the presence of Cu(OAc)(2) and 1,4-benzoquinone in a mixture of propionic acid with diethyl ether gave the corresponding 15,16-distyryl derivative and only traces of 15- and 16-monosubstituted furanolabdanoids. Oxidative coupling of the title compound with methyl acrylate under analogous conditions afforded a mixture of 15-mono-, 16-mono-, and 15,16-dialkenylation products whose ratio changed during the process. The reaction was stereoselective, and the exocyclic double bond in the products had exclusively E configuration.

Cite: Kharitonov Y.V. , Shul'ts E.E. , Shakirov M.M. , Tolstikov G.A.
Synthetic transformations of higher terpenoids: XXV. Cross coupling of phlomisoic acid methyl ester with alkenes in the presence of oxidants
Russian Journal of Organic Chemistry. 2011. V.47. N4. P.602-605. DOI: 10.1134/S107042801104021X WOS Scopus РИНЦ

ArticleLinkType.TRANSLATED_TO_ORIGINAL: Харитонов Ю.В. , Шульц Э.Э. , Шакиров М.М. , Толстиков Г.А.
Синтетические трансформации высших терпеноидов. xxv. кросс-сочетание метилового эфира фломизоиковой кислоты с алкенами в присутствии окислителей
Журнал органической химии (RUSS J ORG CHEM+). 2011. Т.47. №4. С.597-600. РИНЦ

Dates:

Published print:	Apr 1, 2011
Published online:	May 12, 2011

Identifiers:

Web of science	WOS:000290541100021
Scopus	2-s2.0-79957796395
Elibrary	16995668
OpenAlex	W2054408630

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