The Exploitation of Enzymatically-Derived cis-1,2-Dihydrocatechols and Related Compounds in the Synthesis of Biologically Active Natural Products

Abstract

The title compounds of the general form 1 can be produced at large scale and in essentially enantiomerically pure form (when X≠H) through the whole cell biotransformation of the corresponding aromatic. The "dense" and varied functionality associated with these metabolites mean that they have become increasingly useful chirons for the total synthesis of a range of natural product types. This personal account details the outcomes of a nearly three-decade long campaign within our group to exploit these compounds in the synthesis of a diverse range of small molecule natural product targets. The work is subdivided according to the key transformation(s) employed in each synthesis. The development of newer chirons that "complement" the utility of the cis-1,2-dihydrocatechols are also described.

Keywords: Chirons; Cross-couplings; Diels-Alder Reactions; Electrophilic Additions; Eschenmoser-Claisen rearrangements; Natural Products; Oxidative Cleavage; cis-1,2-Dihydrocatechols.