Abstract

The biocatalytically-derived and enantiomerically pure cis-1,2-dihydrocatechols of the general form 1 embody functionalities that can be selectively manipulated in various ways. As a result these compounds have served as highly effective starting materials for the synthesis of a diverse array of structures, including numerous natural products. The latent symmetry elements embodied within many of these compounds together with the capacity to generate new forms of them using directed evolution techniques warrants their consideration as fundamental new building blocks for chemical synthesis.

INTRODUCTION

The chiral pool (or chiron) approach to chemical synthesis remains a profoundly important one for the generation of enantiomerically pure compounds. Carbohydrates, amino acids, terpenes and hydroxyacids have all served as particularly useful members of this pool (1). However, advances in biocatalysis are providing synthetic chemists with a remarkable range of new, structurally fascinating and enantiomerically pure starting materials for the synthesis of a diverse range of target molecules (2). This short review is focussed on introducing the reader to one such group of compounds, namely the cis-1,2-dihydrocatechols (1a–h, Figure 1) (3). Information on the modes of generation of these metabolites, the chemical manipulation of them and the manner in which they can be deployed in the total synthesis of biologically active natural products are presented in the following sections along with key points-of-entry into the substantial body of literature that now exists on this topic.

GENERATION OF CIS-1,2-DIHYDROCATECHOLS
Work carried out in the 1960’s by Gibson et al. (4) established that the bac ...