Synthetic transformations of higher terpenoids: XVII. Intramolecular cyclization of N-furfuryl Amides of the labdane series 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: 2008, Volume: 44, Number: 4, Pages: 516-523 Pages count : DOI: 10.1134/S1070428008040088 | ||
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Abstract:
16-(Benzylaminomethyl)lambertianic acid methyl ester reacts with 2-methylprop-2-enoyl chloride to give unsaturated amide which readily undergoes intramolecular [4+2]-cycloaddition with formation of terpenoid derivatives of 10-oxa-3-azatricyclo[5.2.1.0(1,5)]decenone. Acetylation of lambertianic acid methyl ester with acetic anhydride occurs preferentially at the 2-position of the furan ring and is accompanied by migration of the exocyclic double bond. Reductive amination of 16-acetyl-15,16-epoxylabda-8(9),13,14-triene and subsequent reaction of the resulting amine with 2-methylprop-2-enoyl chloride give intramolecular cyclization products in high yield without isolation of intermediate furfurylacryloyl derivative. Reactions of methyl 16-(benzylaminomethyl)-15,16-epoxylabda-8(9),13,14- and -8(17),13,14-trien-18-oates with maleic anhydride lead to the formation of the corresponding 10-oxa-3-azatricyclo[5.2.1.0(1,5)]dec-8-ene-6-carboxylic acid derivatives as mixtures of diastereoisomers.
Cite:
Kharitonov Y.V.
, Shul'ts E.E.
, Shakirov M.M.
, Tolstikov G.A.
Synthetic transformations of higher terpenoids: XVII. Intramolecular cyclization of N-furfuryl Amides of the labdane series
Russian Journal of Organic Chemistry. 2008. V.44. N4. P.516-523. DOI: 10.1134/S1070428008040088 WOS Scopus РИНЦ OpenAlex
Synthetic transformations of higher terpenoids: XVII. Intramolecular cyclization of N-furfuryl Amides of the labdane series
Russian Journal of Organic Chemistry. 2008. V.44. N4. P.516-523. DOI: 10.1134/S1070428008040088 WOS Scopus РИНЦ OpenAlex
Original:
Харитонов Ю.В.
, Шульц Э.Э.
, Шакиров М.М.
, Толстиков Г.А.
Синтетические трансформации высших терпеноидов xvii.* внутримолекулярная циклизация фурфуриламидов лабданового типа
Журнал органической химии (RUSS J ORG CHEM+). 2008. Т.44. №4. С.521-528. РИНЦ
Синтетические трансформации высших терпеноидов xvii.* внутримолекулярная циклизация фурфуриламидов лабданового типа
Журнал органической химии (RUSS J ORG CHEM+). 2008. Т.44. №4. С.521-528. РИНЦ
Dates:
| Published print: | Apr 1, 2008 |
| Published online: | Jun 3, 2008 |
Identifiers:
| Web of science: | WOS:000256232700008 |
| Scopus: | 2-s2.0-44649193079 |
| Elibrary: | 13573660 |
| OpenAlex: | W2074756421 |