A Novel Geiparvarin Analogue Possessing a Fluorinated Segment

Abstract

Starting from the 4-(ω-iodoperfluorobutyl)-2-methylbut-3-yn-2-ol, the 5-(ω-iodoperfluoropropyl)furan-3(2H)-one is formed in one step under the Rupe conditions (reflux with formic acid, yield 93%). This compound is added to 2-methylbut-3-yn-2-ol through a radical chain process, using the Huang system (Na₂S₂O₄-NaHCO₃, MeCN-H₂O), yielding the expected adduct (47%), the hydrodeiodinated equivalent compound (35%) and a new spiro compound containing a partly fluorinated ring (18%). This latter compound may result from an interesting annulation process. The iodo adduct is hydrodeiodinated (Zn-AcOH-EtOH, final yield 82%) and added to umbelliferone through Mitsunobu etherification (PPh₃-DIAD-THF) yielding (45%) the expected Geiparvarin analogue possessing a fluorinated segment

Key words

Geiparvarin - antitumour agents - fluorine - furans - annulations - spiro compounds - DNA

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