Fluorinated Natural Products: Occurrence and Biosynthesis

Abstract

Despite the abundance of fluorine in the Earth’s crust naturally occurring organofluorine compounds are comparatively rare in nature with those isolated to date totalling no more than about a dozen confined to a few plants and two species of bacteria. Notwithstanding considerable interest and a variety of speculative suggestions, the mechanism of biological C-F bond formation is still unknown, although significant progress has been made in elucidating the pathway by which biosynthesis of fluoroacetate and 4-fluorothreonine occurs in the bacterium Streptomyces cattleya. In this chapter we review the nature and distribution of organofluorine compounds formed biologically and discuss the progress made in our understanding of C-F bond biosynthesis over the 60 years since fluoroacetate was first identified as a natural product.