Unexpected Rearrangement and Aromatization on Dehydration Reaction of the Bioactive Diterpenequinone 7α-Hydroxyroyleanone

7a-Hydroxyroyleanone is a bioactive diterpene isolated from leaves of Tetradenia riparia, active against tuberculosis and T. cruzi. In order to use this compound as starting material for the synthesis of compounds with enhanced bioactivity we aimed the dehydration of the 7-alpha-hydroxyl group of ro...

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Bibliographic Details
Published in:Journal of the Brazilian Chemical Society 2020-03, Vol.31 (3), p.597-602
Main Authors: Leitão, Gilda, Pinheiro, Aline, Rezende, Victor, Silva, Raphael, Paula, Leonardo, Soares, Deivid, Saraiva, Elvira
Format: Article
Language:English
Subjects:
CHEMISTRY, MULTIDISCIPLINARY
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Summary:7a-Hydroxyroyleanone is a bioactive diterpene isolated from leaves of Tetradenia riparia, active against tuberculosis and T. cruzi. In order to use this compound as starting material for the synthesis of compounds with enhanced bioactivity we aimed the dehydration of the 7-alpha-hydroxyl group of royleanone. The reaction performed in acetic acid and hydrochloric acid under reflux gave an unexpected chlorinated naphtoquinone, with aromatization and opening of one of the rings of the starting material, as major product, besides 6,7-dehydroroyleanone and a complex mixture of other products. The reaction products were purified by high-speed countercurrent chromatography with hexane-acetonitrile 1:1. Compounds were tested for their anti-leishmanial activity (L. amazonensis) pointing out a potential leishmanicidal agent which may favor the development of more effective therapies.
ISSN:0103-5053
1678-4790
DOI:10.21577/0103-5053.20190223