A chemoenzymatic synthesis of the carbobicyclic core associated with CP-225,917 and CP-263,114 (phomoidrides A and B)

Abstract

The bromobenzene-derived and enantiopure cis-1,2-dihydrocatechol 3 has been converted, via a reaction sequence involving Diels-Alder cycloaddition, anionic oxy-Cope rearrangement and Wolff ring-contraction steps, into compound 4 and epimer 24, which embody key structural elements associated with the nonadride-type natural products CP-225,917 (1) and CP-263,114 (2).