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Recent progress in the synthesis of promising bicyclo[4.3.1]decanes by the oxidative rearrangement reaction of bicyclo[4.2.2]decatetraenes
* 1 , 2 , 2
1  Institute of Petrochemistry and Catalysis of Russian Academy of Sciences
2  N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Academic Editor: Julio A. Seijas (registering DOI)

Data on the synthesis of practically important bicyclo[4.3.1]decatrienes based on oxidative transformations of bicyclo[4.2.2]deca-2,4,7,9-tetraenes are summarized. The authors have shown for the first time that the reactions of electrophilic activation of double bonds in bicyclo[4.2.2]deca-2,4,7,9-tetraenes under the action of m-chloroperbenzoic acid are accompanied by oxidative skeletal rearrangement with the formation of bicyclo[4.3.1]deca-2,4,8-triene-7,10-diols. A probable mechanism for the detected rearrangement is proposed. Data on the study of the antitumor properties of the resulting bicyclo[4.3.1]decatrienes are presented, among which samples with high antitumor activity were identified.

Keywords: 1,3,5,7-cyclooctatetraene; [6+2]-cycloaddition; bicyclo[4.2.2]deca-2,4,7,9-tetraene; oxidative rearrangement; bicyclo[4.3.1]deca-2,4,8-triene-7,10-diol; antitumor activity