3 years ago

Total Synthesis of Two 8-Oxoprotoberberine Alkaloids: Alangiumkaloids A and B

Minoru Ishikura, Yoshiyuki Shigemori, Mizuki Taketomi, Noriyuki Hatae, Rika Kotouge, Miharu Hironaka, Takashi Nishiyama, Eri Taguchi, Tominari Choshi
A new and versatile synthetic route for 8-oxoprotoberberine 17 via the synthesis of isoquinolinone 16 and construction of a B-ring is described. The key step is the synthesis of isoquinolinone 14 through thermal cyclization of 2-alkynylbenzaldehyde oxime 12 to afford isoquinoline N-oxide 13, followed by a Reissert-Henze-type reaction. The first total synthesis of 8-oxoprotoberberine alkaloid alangiumkaloids A and B was achieved by using this strategy.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/ejoc.201701557

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