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Communication | Regular issue | Vol 14, No. 1, 1980, pp.11-14
Published online, 1st January, 1970
DOI: 10.3987/R-1980-01-0011
Total Synthesis of Pseudo Type Protopine Alkaloids

Kazuhiko Orito,* Shigekazu Kudoh, Kinji Yamada, and Mitsuomi Itoh

*Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Kita 13 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0828, Japan


Photolysis of the chloroacetamides (1) gave the benzazepinones (2), whose benzyl derivatives (3) were cyclized to the benz[d]indeno[1,2-b]azepines (4) by treatment with phosphoryl chloride. Dye-sensitized photo-oxygenation of 4, followed by lithium aluminum hydride reduction and manganese dioxide oxidation of the products 5, led to a total synthesis of pseudoprotopine (7a) and fagarine II (7b) as well as their analogs 7c and 7d.