Chapter 2 - Enzymatic dihydroxylation of aromatic compounds: Nature's unique reaction and its impact on the synthesis of natural products

Abstract

The chemoenzymatic dihydroxylation of arenes by microbial organisms represents a unique reaction found in nature. The reaction is highly stereo-, regio-, and enantioselective and yields versatile metabolites that have been exploited in the synthesis of countless natural products and useful homochiral building blocks. This chapter provides a brief history of the discovery and development of the microbial diol metabolites, their synthetic utility, and evolving applications in total synthesis. An extensive table is included to depict the many natural products and related synthetic targets attained through syntheses starting from cis-dihydrocatechols. The authors hope to highlight the utility of these chiral synthons in the assembly of natural products and to demonstrate the importance of incorporating biological methods into enantioselective synthesis.