A furan Diels-Alder cycloaddition approach to scyphostatin analogues.

The synthesis of two diastereoisomers of the epoxycyclohexenone core of scyphostatin, a naturally occurring sphingomyelinase inhibitor, has been achieved via a common oxabicyclic intermediate. The diastereomeric intermediates are accessed by stereodivergent oxidative functionalisation processes, followed by a Lewis acid mediated ring opening rearrangement reaction.