Biocatalysis as the strategy of choice in the exhaustive enantiomerically controlled synthesis of conduritols

Abstract

An approach to several conduritols, both naturally occurring and unnatural derivatives, is described. The key strategy of this potentially exhaustive approach relies on the bio-oxidation of chloro- or bromobenzene to their corresponding cis-diols. Subsequent synthetic manipulations enjoy extensive use of symmetry considerations in the introduction of functionalities. Complete stereo- and enantio-control is achieved in the preparation of conduritols E 5 and F 6, aminoconduritols A-1 7 and F-4 9, fluorodeoxyconduritol F 13, chlorodeoxyconduritol F 14, and deoxyconduritol E 15. A detailed discussion of the stereoelectronic parameters that control opening of epoxy alkenes of type 33 or 37 is advanced. Full experimental details are provided for all compounds.