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

被引：75

作者：

Harayama, T ^{[1
]}

Hori, A ^{[1
]}

Serban, G ^{[1
]}

Morikami, Y ^{[1
]}

Matsumoto, T ^{[1
]}

Abe, H ^{[1
]}

Takeuchi, Y ^{[1
]}

机构：

[1] Okayama Univ, Fac Pharmaceut Sci, Okayama 7008530, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 47期

关键词：

palladium; cytotoxic activity; DNA topoisomerase inhibitor; pyrroloquinazolinequinoline alkaloid; indolopyridoquinazoline alkaloid;

D O I：

10.1016/j.tet.2004.09.016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of luotonin A was achieved in excellent yield by using a Pd-assisted biaryl coupling reaction of N-(bromoquinolinyl)methylquinazolinone with Cy3P and KOAc. The successive treatment of luotonin A with NBS and aq. AgNO3 gave luotonin B in good yield. Although the Pd-assisted coupling reaction of N-(2-bromoindolyl)ethylquinazolinone with Cy3P and KOAc yielded rutaecarpine, in poor yield, N-acetate under the same reaction conditions yielded the desired rutaecarpine directly in excellent yield. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：10645 / 10649

页数：5

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