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.
- Cytotoxic activity
- DNA topoisomerase inhibitor
- Indolopyridoquinazoline alkaloid
- Pyrroloquinazolinequinoline alkaloid
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry