Directed joint total synthesis of the three naphthylisoquinoline alkaloids dioncolactone A, dioncopeltine A, and 5'-O-demethyldioncophylline A

Article abstract of DOI:10.1016/S0040-4020(98)01040-0

The first total synthesis of the three antimalarial naphthylisoquinoline alkaloids dioncolactone A (4), dioncopeltine A (5), and 5'-O- demethyldioncophylline A (6) is described. The regio- and stereoselective construction of the biaryl axes was achieved through the 'lactone methodology', by ester-type prefixation of the two molecular moieties, intramolecular coupling, and atropo-diastereoselective cleavage of the lactone auxiliary bridge. As a novel alternative, the configuration at the axis may be installed by atroposelective hydroxy aldehyde reduction through dynamic kinetic resolution.