SYNTHESIS OF BENZOILFLOROGLUCINOLPOLYPRENYLATED COMPOUNDS. TRAINING STUDIES OF THE BICYCLE SYSTEM [3.3.1] NONANO-2,4,9-TRIONA

Abstract

Polycyclic polyprenylated acylphloroglucinol compounds (PPAPs) are a family of natural products with interesting biological properties, coming from the plant family Clusiaceae. This class of compounds is characterized by having a unique bicyclic structure of acylfloroglucinol, whose base skeleton, the bicyclo [3.3.1] nonane-2,4,9- triona, has sparked renewed interest among synthetic and pharmaceutical chemists. The evaluation of a mixture of xanthochimol and gutiferone E (type B PPAPs) from the ethylacetic extract of the Garcinia pyrifera in the test of depolymerization of microtubules in tubulin, was similar to the response displayed by paclitaxel, a reference antitumor agent in the breast cancer cell line. By virtue of this result encouraging, hemisynthesis work was started with a view to carrying out a study of biological structure-activity, which gave lead to derivatives lacking in vitro activity. For this reason and given the need to deepen our knowledge of the structural requirements necessary in the mechanism of action on the tubulin-microtubule system, have been carried out significant efforts towards obtaining PPAPs compounds via total synthesis.