期刊
ORGANIC LETTERS
卷 18, 期 20, 页码 5280-5283出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b02597
关键词
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资金
- National Research Foundation of Korea (NRF) - Korean Government [NRF-2015R1D1A1A01057200, NRF-20100020209]
- NRF - Korean Government [NRF-2014-011165]
- Center for New Directions in Organic Synthesis
The total synthesis of rutaecarpine (1) and luotonin A (2) is described through controlled cyclization of a common aldimine intermediate derived from qethyl-2-aminocinnamate and quinazolinone-2-carbaldehyde. The cyanide -mediated imino-Stetter reaction of aldimine 5 provided the corresponding indole derivative 3, from which the total synthesis of rutaecarpine (1) was completed via the formation of a 6-membered C-ring. On the other hand, microwave assisted thermal 6 pi-electrocyclization of the common intermediate 5, followed by the formation of a 5-membered C'-ring, allowed the completion of the total synthesis of luotonin A (2).
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