2010 Fiscal Year Final Research Report
A new synthetic development of the bioactive benzo[c]phenanthridines based on a microwave-assisted electrocyclic reaction of aza 6π-electron system
| Project/Area Number |
20590026
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Fukuyama University |
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Principal Investigator |
SATOSHI Hibino Fukuyama University, 薬学部, 教授 (60112885)
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| Co-Investigator(Kenkyū-buntansha) |
CHOSHI Tominari 福山大学, 大学院・薬学研究科・薬学部, 准教授 (10248297)
SHUHEI Azuma 福山大学, 薬学部, 助手 (30509287)
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| Project Period (FY) |
2008 – 2010
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| Keywords | benzo[c]phenanthridine alkaloid / 電子環状反応 / アザ6π電子系 / マイクロ波照射 / β-テトラロン / nornitidine / noravicine / isodecarine / norsanguinarine / norchelerythrine / zanthoxyline / broussonpapyrine / chelerythrine / X-線結晶構造解析 |
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| Research Abstract |
Total syntheses of the nor-type of benzo[c]phenanthridine alkaloids, nornitidine, noravicine, isodecarine, norchelerythrine, norsanguinarine, and zanthoxyline, and benzo[c]phenanthridine alkaloids, nitidine, avicine, sanguinarine, chelerythrine and broussonpapyrine were achieved. The key step was the construction of tetracyclic 11,12-dihydrobenzo[c]phenanthridine using a microwave-assisted electrocyclic reaction of the 2-cycloalkenylbenzaldoxime methyl ether as an aza 6π-electron system, which was derived in two steps from a Suzuk-Miyaura cross-coupling reaction of 2-brombenzaldehyde with (3,4-dihydro-6,7-methylenedioxynaphthyl)boronic acid pinacol ester. In addition, the exact structure of broussonpapyrine was determined to be chelerythrine by NMR spectral analysis.
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