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- Title
Synthetic transformations of higher terpenoids: XVII. Intramolecular cyclization of N-furfuryl amides of the labdane series.
- Authors
Kharitonov, Yu. V.; Shul'ts, E. E.; Shakirov, M. M.; Tolstikov, G. A.
- 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[5.2.1.01,5]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[5.2.1.01,5]dec-8-ene-6-carboxylic acid derivatives as mixtures of diastereoisomers.
- Subjects
AMIDES; CARBAMAZEPINE; NITROSAMIDES; POLYAMIDES; TERPENES; LIPIDS; HYDROCARBONS
- Publication
Russian Journal of Organic Chemistry, 2008, Vol 44, Issue 4, p516
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428008040088