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Directed ortho Metalation Approach to C-7-Substituted Indoles. Suzuki−Miyaura Cross Coupling and the Synthesis of Pyrrolophenanthridone Alkaloids

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posted on 01.05.2003, 00:00 by Christian G. Hartung, Anja Fecher, Brian Chapell, Victor Snieckus
Although the indole N-phosphinoyl derivative 4 undergoes n-BuLi deprotonation/electrophile quench to afford C-7-substituted products, its deprotection requires harsh conditions. On the other hand, the N-amide 12, upon sequential or one-pot C-2 metalation, silylation, C-7 metalation, and electrophile treatment, furnishes indoles 7 in good overall yields. In combination with the Suzuki−Miyaura protocol, C-7 aryl (heteroaryl)-substituted indoles 14 and 16 are obtained, including hippadine and pratosine, members of the pyrrolophenanthridone alkaloid family.