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

71 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

Fingerprint

Quinazolines
Alkaloids
Acetates
luotonin A
rutecarpine
luotonin B

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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

Concise synthesis of quinazoline alkaloids, luotonins A and B, and rutaecarpine. / Harayama, Takashi; Hori, Akihiro; Serban, Georgeta; Morikami, Yoshiaki; Matsumoto, Takuya; Abe, Hitoshi; Takeuchi, Yasuo.

In: Tetrahedron, Vol. 60, No. 47, 15.11.2004, p. 10645-10649.

Research output: Contribution to journalArticle

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, vol. 60, no. 47, pp. 10645-10649. https://doi.org/10.1016/j.tet.2004.09.016
Harayama T, Hori A, Serban G, Morikami Y, Matsumoto T, Abe H et al. Concise synthesis of quinazoline alkaloids, luotonins A and B, and rutaecarpine. Tetrahedron. 2004 Nov 15;60(47):10645-10649. https://doi.org/10.1016/j.tet.2004.09.016
Harayama, Takashi ; Hori, Akihiro ; Serban, Georgeta ; Morikami, Yoshiaki ; Matsumoto, Takuya ; Abe, Hitoshi ; Takeuchi, Yasuo. / Concise synthesis of quinazoline alkaloids, luotonins A and B, and rutaecarpine. In: Tetrahedron. 2004 ; Vol. 60, No. 47. pp. 10645-10649.
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