Synthetic transformations of higher terpenoids: XXV. Cross coupling of phlomisoic acid methyl ester with alkenes in the presence of oxidants Full article
| Journal |
Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393 |
||
|---|---|---|---|
| Output data | Year: 2011, Volume: 47, Number: 4, Pages: 602-605 Pages count : DOI: 10.1134/S107042801104021X | ||
| Authors |
|
||
| Affiliations |
|
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 OpenAlex
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 OpenAlex
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
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 |