COMBINED DIRECTED ORTHO-METALATION CROSS-COUPLING STRATEGIES - DESIGNFOR NATURAL PRODUCT SYNTHESIS

Recent efforts in our laboratories have established connections betwee n the Directed ortho Metalation (DoM) (Scheme 1) and transition metal catalyzed cross coupling (Scheme 2) strategies. The combination of the se with the Remote Metalation (Scheme 4) tactic has led to the evoluti on of powerful new methods for aromatic synthesis. The application of these concepts, singularly or combined, for the construction of alkalo ids (Scheme 6), fluorenone natural products (Schemes 7, and 8), naphth obenzopyranones (Schemes 9 and 10), and naturally-occurring phenanthre nes is given as illustration of the new synthetic aromatic chemistry.