2006 Fiscal Year Final Research Report Summary
Deve I opment of Practical Radical Reaction and its Applicat i on to the Synthesis of Physiologically Active Compounds
| Project/Area Number |
16390004
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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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 | Kanazawa University |
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Principal Investigator |
ISHIBASHI Hiroyuki Graduate School of Natural Science and Technology., Professor, 自然科学研究科, 教授 (70028869)
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| Co-Investigator(Kenkyū-buntansha) |
UCHIYAMA Masahiko Advanced Science Research Center., Associate Professor, 学際科学実験センター, 助教授 (40277265)
MATSUO Jun-ichi Graduate School of Natural Science and Technology, Associate Professor, 自然科学研究科, 助教授 (50328580)
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| Project Period (FY) |
2004 – 2006
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| Keywords | enamide / radical cyclization / stemonamide / radical cascade / single electron transfer / lennoxamine / cylindricine / cephalotaxine |
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| Research Abstract |
1. Radical cascade involving 6-endo selective cyclization of aryl radical onto olefinic bond of enamide and 5-endo cyclization of the resulting amidoyl radical afforded a convenient synthesis of phenanthroindolizidines containing a methyl group at their C13 position.
2. Radical cascade involving 6-endo selective cyclization of alkyl radical onto olefinic bond of enamide and 5-endo cyclization of the resulting amidoyl radical afforded a convenient synthesis of cylindricine skeleton.
3. Radical cascade involving 7-endo selective cyclization of aryl radical onto olefinic bond of enamide and 5-endo cyclization of the resulting amidoyl radical afforded a concise synthesis of cephalotoxine skeleton.
4. Radical cascade involving 7-endo selective cyclization of aryl radical onto olefinic bond of enamide and homolytic aromatic substitution of the resulting amidoyl radical afforded a short synthesis of lennoxamine.
5. Radical cascade involving 7-endo selective cyclization of alkyl radical onto olefinic bond of enamide and 5--endo cyclization of the resulting amidoyl radical afforded a total synthesis of stemonamide, isostemonamide, stemonamine, and isostemonamine.
6. N-Allylic or N-vinylic, α, α, α-trichloroacetamides, upon heating in 1, 4-dimethylpiperazine, underwent radical cyclization to give the corresponding y-lactams.
7. exo and endo Selectivities of aryl or alkyl radical onto olefinic bond of enamides were studied in detail.
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