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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
Published:
14 November 2022
by MDPI
in The 26th International Electronic Conference on Synthetic Organic Chemistry
session Bioorganic, Medicinal and Natural Products Chemistry
https://doi.org/10.3390/ecsoc-26-13539
(registering DOI)
Abstract:
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
