The directed ortho metalation - cross coupling symbiosis. Regioselective methodologies for biaryls and heterobiaryls. Deployment in aromatic and heteroaromatic natural product synthesis

摘要

In this mini-review, synthetic methods for biaryls and heterobiaryls interconnecting the directed ortho metalation (DoM) reaction with Corriu-Kumada, Negishi, Suzuki-Miyaura and, less, Stille cross coupling reactions are presented from perspectives of development of new reaction parameters (Suzuki-Miyaura: Schemes 4-7), new cross coupling partners (Corriu-Kumada: Schemes 9 and 11), and comprehensive evaluation (Schemes 12 and 13). Recent work on the application of these protocols to indole derivatives (Schemes 16-18), dibenzopyranones (Scheme 19), aza- and isoazacoumestans (Scheme 20), and kinamycin antibiotics (Scheme 21) is described. (C) 2002 Elsevier Science B.V. All rights reserved. [References: 64]