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Synthesis 2001; 2001(3): 0444-0450
DOI: 10.1055/s-2001-11424
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Total Synthesis of Benzo[c]phenanthridine Alkaloids, Chelerythrine and 12-Methoxydihydrochelerythrine, by a Palladium-Assisted Internal Biaryl Coupling Reaction

Takashi Harayama* , Toshihiko Akiyama, Hirashi Akamatsu, Kazuko Kawano, Hitoshi Abe, Yasuo Takeuchi
  • *Faculty of Pharmaceutical Sciences, Okayama University, Tsushima-naka 1-1-1, Okayama 700-8530, Japan; Fax + 81(86)2 51 79 63; E-mail: harayama@pharm.okayama-u.ac.jp
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Publication Date:
31 December 2001 (online)

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A convenient and versatile synthesis of benzo[c]phenanthridine alkaloids, chelerythrine (1) and 12-methoxydihydrochelerythrine (5), was accomplished via an internal aryl-aryl coupling reaction of haloamides 8 and 9 by a palladium-assisted cyclization reaction.

alkaloids - internal aryl-aryl coupling - ring closure - Heck-type reaction - palladium - haloamides