An efficient formal synthesis of balanol via the asymmetric epoxide ring opening reaction

Article abstract of DOI:10.1016/S0040-4039(97)00192-5

An efficient formal synthesis of balanol is described. The thirteen-step sequence features a highly enantioselective (92% ee) ring opening of 1,4-cyclohexadiene monoepoxide with TMSN₃ catalyzed by the Cr-salen complex 3. A selective Beckmann rearrangement followed by amide reduction and nitrogen functionalization affords 2, thus completing a formal synthesis of balanol in 31% overall yield.