Russian Journal of Organic Chemistry

, Volume 44, Issue 4, pp 516–523 | Cite as

Synthetic transformations of higher terpenoids: XVII. Intramolecular cyclization of N-furfuryl amides of the labdane series

  • Yu. V. Kharitonov
  • E. E. Shul’ts
  • M. M. Shakirov
  • G. A. Tolstikov


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]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]dec-8-ene-6-carboxylic acid derivatives as mixtures of diastereoisomers.


Maleic Anhydride Intramolecular Cyclization Furan Ring Oily Substance Benzylamino 
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Copyright information

© MAIK Nauka 2008

Authors and Affiliations

  • Yu. V. Kharitonov
    • 1
  • E. E. Shul’ts
    • 1
  • M. M. Shakirov
    • 1
  • G. A. Tolstikov
    • 1
  1. 1.Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian DivisionRussian Academy of SciencesNovosibirskRussia

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