88720-89-2Relevant academic research and scientific papers
Directed ortho metalation approach to C-7-substituted indoles. Suzuki-Miyaura cross coupling and the synthesis of pyrrolophenanthridone alkaloids
Hartung, Christian G.,Fecher, Anja,Chapell, Brian,Snieckus, Victor
, p. 1899 - 1902 (2007/10/03)
(Matrix presented) 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.
A new approach to pyrrolophenanthridone alkaloids via intramolecular radical cyclization
Tsuge, Otohiko,Hatta, Taizo,Tsuchiyama, Hiroshi
, p. 155 - 156 (2007/10/03)
A new approach to the synthesis of pyrrolophenanthridone class of alkaloids is described. The method is based on intramolecular radical cyclization of easily accessible 1-aroyl-7-bromoindoles with Bu3SnH and AIBN.
A synthesis of the amaryllidaceae alkaloid pratosine
Pereira, M. Manuela A.,Prabhakar, Sundaresan,Lobo, Ana M.
, p. 744 - 747 (2007/10/03)
A synthesis of pratosine by thermolysis of the Michael adduct obtained from 5-hydroxy-8,9-dimethoxy-6(5H)-phenanthridone and methyl propiolate is described.
