Synthesis of Organofluorine Compounds

Fluoroorganic chemistry is virtually a man-made subject. Indeed, perfluorocarbon chemistry—which straddles organic and inorganic chemistry—is sometimes facetiously referred to as unnatural product chemistry. Fluorometabolites do occur in nature, but they are few in number and only monofluorides have been detected so far.1 The best known is the plant metabolite CH2FCO2H (see Chapter 1); the other nine include the related compounds CH2FCOCH3, 2-fluorocitric acid, F(CH2) n CO2H (n = 9, 13, 15), and F(CH2)8CH=CH(CH2)7CO2H. The most intriguing by far is nucleo-cidin (1), an antibiotic fluoro-sugar derivative produced by the microorganisms Streptomyces calvus.