Staunton-Weinreb annulation

Tandem Michael—Dieckmann/Claisen reaction of ortho-toluates The Staunton—Weinreb annulations 13T3747. 

The atroposelective construction of the 6,6 -biaryl linkage was recognized as the key step in the synthesis of viriditoxin. Although many atroposelective couplings of complex molecules have been completed and have been the subject of many reviews,most of these approaches relied on either proximal stereogenic centers or covalently linked chiral auxiliaries. Our objective was to explore the influence of distal chiral centers on the catalytic oxidative dimerization of naphthopyran-2-ones using vanadium catalysis (Scheme 7). Assembly of naphthopyran-2-ones has been well studied and recently reviewed." The Staunton-Weinreb annulation or the Michael-Dieckmann condensation is ideally suited for the rapid... 

The regioselective synthesis of complex aromatic compounds has been an important and active research area for chemists over decades. Various strategies and documented synthetic methods have found favor for the synthesis of aromatic compounds. These would include the use of Diels-Alder reactions, Friedel-Crafts methodology, and a range of annulation methods such as those developed by Hauser, Kraus, Staunton, and Weinreb, as well as a range of transition... 

---