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

ArticleLinkType.TRANSLATED_TO_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

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

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