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

doi:10.1016/j.tet.2004.09.016

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

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78 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 language	English
Pages (from-to)	10645-10649
Number of pages	5
Journal	Tetrahedron
Volume	60
Issue number	47
DOIs	https://doi.org/10.1016/j.tet.2004.09.016
Publication status	Published - 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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10.1016/j.tet.2004.09.016

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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.",

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T1 - Concise synthesis of quinazoline alkaloids, luotonins A and B, and rutaecarpine

AU - Harayama, Takashi

AU - Hori, Akihiro

AU - Serban, Georgeta

AU - Morikami, Yoshiaki

AU - Matsumoto, Takuya

AU - Abe, Hitoshi

AU - Takeuchi, Yasuo

PY - 2004/11/15

Y1 - 2004/11/15

N2 - 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.

AB - 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.

KW - Cytotoxic activity

KW - DNA topoisomerase inhibitor

KW - Indolopyridoquinazoline alkaloid

KW - Palladium

KW - Pyrroloquinazolinequinoline alkaloid

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

Abstract

Keywords

ASJC Scopus subject areas

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