Tetrahydrofuran containing acetogenins (THF-AGEs) are a naturally occurring class of compounds that are potently toxic to a wide range of human tumor cell lines, including multi-drug resistant (MDR) strains. In this context more easily accessed THF-AGE’s are of interest for evaluation as clinical agents. To this end we devised a cross-metathesis based modular synthesis of the mono-THF-AGE 4-deoxyannonacin (4-DAN), and applied this strategy to a library of analogues of 4-DAN with a carbohydrate moiety, and a piperazine or a O-butyl residue, as substitutes for the THF and butenolide segments respectively. The synthesis and antitumor properties of these new analogues will be presented.

Synthesis and antitumor activity of mimics of the tetrahydrofuran containing acetogenins

255th National Meeting (2018)

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