Concise synthesis of quinazoline alkaloids, luotonins A and B, and rutaecarpine

Takashi Harayama, Akihiro Hori, Georgeta Serban, Yoshiaki Morikami, Takuya Matsumoto, Hitoshi Abe, Yasuo Takeuchi

Research output: Contribution to journalArticle

73 Citations (Scopus)

Abstract

The total synthesis of luotonin A was achieved in excellent yield by using a Pd-assisted biaryl coupling reaction of N-(bromoquinolinyl)methylquinazolinone with Cy 3P and KOAc. The successive treatment of luotonin A with NBS and aq. AgNO 3 gave luotonin B in good yield. Although the Pd-assisted coupling reaction of N-(2-bromoindolyl)ethylquinazolinone with Cy 3P and KOAc yielded rutaecarpine in poor yield, N-acetate under the same reaction conditions yielded the desired rutaecarpine directly in excellent yield. Graphical Abstract.

Original languageEnglish
Pages (from-to)10645-10649
Number of pages5
JournalTetrahedron
Volume60
Issue number47
DOIs
Publication statusPublished - Nov 15 2004

Keywords

  • Cytotoxic activity
  • DNA topoisomerase inhibitor
  • Indolopyridoquinazoline alkaloid
  • Palladium
  • Pyrroloquinazolinequinoline alkaloid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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  • Cite this

    Harayama, T., Hori, A., Serban, G., Morikami, Y., Matsumoto, T., Abe, H., & Takeuchi, Y. (2004). Concise synthesis of quinazoline alkaloids, luotonins A and B, and rutaecarpine. Tetrahedron, 60(47), 10645-10649. https://doi.org/10.1016/j.tet.2004.09.016