Synthetic transformations of higher terpenoids: XXXII. Synthesis of 16-alkenyl-substituted labdatrienes by oxidative coupling of methyl phlomisoate with alkenes Full article
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Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393 |
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| Output data | Year: 2013, Volume: 49, Number: 11, Pages: 1690-1702 Pages count : 13 DOI: 10.1134/S1070428013110225 | ||
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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.
Cite:
Kharitonov Y.V.
, Kremenko O.I.
, Shults E.E.
, Shakirov M.M.
, Tolstikov G.A.
Synthetic transformations of higher terpenoids: XXXII. Synthesis of 16-alkenyl-substituted labdatrienes by oxidative coupling of methyl phlomisoate with alkenes
Russian Journal of Organic Chemistry. 2013. V.49. N11. P.1690-1702. DOI: 10.1134/S1070428013110225 WOS Scopus РИНЦ
Synthetic transformations of higher terpenoids: XXXII. Synthesis of 16-alkenyl-substituted labdatrienes by oxidative coupling of methyl phlomisoate with alkenes
Russian Journal of Organic Chemistry. 2013. V.49. N11. P.1690-1702. DOI: 10.1134/S1070428013110225 WOS Scopus РИНЦ
ArticleLinkType.TRANSLATED_TO_ORIGINAL:
Харитонов Ю.В.
, Брусенцева О.И.
, Шульц Э.Э.
, Шакиров М.М.
, Толстиков Г.А.
Синтетические трансформации высших терпеноидов. xxxii. синтез 16-алкенилзамещенных лабдатриенов реакцией окислительного сочетания метилового эфира фломизоиковой кислоты с алкенами
Журнал органической химии (RUSS J ORG CHEM+). 2013. Т.49. №11. С.1707-1718. РИНЦ
Синтетические трансформации высших терпеноидов. xxxii. синтез 16-алкенилзамещенных лабдатриенов реакцией окислительного сочетания метилового эфира фломизоиковой кислоты с алкенами
Журнал органической химии (RUSS J ORG CHEM+). 2013. Т.49. №11. С.1707-1718. РИНЦ
Dates:
| Published print: | Nov 1, 2013 |
| Published online: | Dec 11, 2013 |
Identifiers:
| Web of science | WOS:000328263200022 |
| Scopus | 2-s2.0-84892956585 |
| Elibrary | 21909438 |
| OpenAlex | W2072536541 |