Progress towards the synthesis of selectively fluorinated curcumin analogues, using various methods of indirect aromatic fluorination is reported.  Curcumin, a constituent of the widely used natural product turmeric, has been shown to possess significant biological properties including anti-cancer, antioxidant, and anti-inflammatory activity.  It suffers significantly from poor bioavailability, however, and often requires huge dosages to obtain significant medicinal benefit.  Replacing one or more hydrogens with fluorine has become an increasingly common and beneficial approach to seeking enhanced bioavailability in pharmaceuticals.  Novel methods of fluorinating vanillin, a key building block in the total synthesis of curcumin, including extensive work using Selectfluor will be reported.  The fluorinated vanillins will be used to prepare fluorinated curcumin analogues bearing one fluorine atom on each ring providing a way to attempt to make the well-documented properties of curcumin more accessible.

Preparation of fluorinated vanillins:  Efforts towards selectively fluorinated curcumins

247th National Meeting (2014)

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