Synthetic studies on azadirachtin (Part 3): Asymmetric synthesis of the tricyclic dihydrofuran moiety of azadirachtin

Article abstract of DOI:10.1016/S0040-4039(99)00040-4

An asymmetric synthesis of the tricyclic dihydrofuran moiety of azadirachtin is reported. The Diels-Alder adduct, which was catalyzed by Evans' chiral Cu-bisoxazoline complex, was easily converted to the tricyclic portion via SmI₂ reductive cleavage and selective functionalization.