Abstract
Abstract:
A short chemoenzymatic route to two natural products—the first, a constituent of Jamaican rum and the second the (+)-antipode of the gibberelin synergist (−)-Pestalotin—was accomplished based on an enzyme-triggered cascade-reaction. Thus, a racemic halomethyl oxirane was hydrolyzed by bacterial epoxide hydrolases to furnish the corresponding vic-halomethyl-diol, which underwent spontaneous ring-closure to furnish an epoxy alcohol in up to 93% e.e. and ≥99 d.e. Due to the fact that this process was enantioconvergent, the occurrence of the undesired enantiomer was entirely avoided. [Copyright &y& Elsevier]
