Total Synthesis of (-)-Haouamine B Pentaacetate and Structural Revision of Haouamine B

The enantiocontrolled total synthesis of (-)-haouamine B pentaacetate was accomplished via an optically active indane-fused beta-lactam, which was prepared by a newly developed Friedel-Crafts reaction. Subsequent cleavage of the beta-lactam and an intramolecular McMurry coupling reaction provided the core indane-fused tetrahydropyridine, which led to the elucidation of the structure, as proposed by Trauner and Zubia.