2013 Fiscal Year Final Research Report
Highly selective synthetic organic reaction using cyclopropane ring opening
| Project/Area Number |
23550048
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Shinshu University |
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Principal Investigator |
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| Project Period (FY) |
2011 – 2013
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| Keywords | シクロプロパン / ジヒドロナフタレン / パラジウム触媒 / 根岸カップリング / 有機分子触媒 / 不斉シクロプロパン化 / 環拡大 / 天然物全合成 |
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| Research Abstract |
1) We achieved the chirality exchange benzannulation from sp3 central chirality to axial chirality, and obtained axially chiral 1-arylnaphthalenes with excellent enantioselectivity. Total synthesis of optically active Procunphthalide was demonstrated by using the chirality exchange benzannulation. 2) A novel ring-expansion of methyl (arylhydroxymethyl)- cyclopropanecarboxylates using Sc(OTf)3 or BF3 afforded 1,2-dihydronaphthalene-3-carboxylic acid ester in high to excellent yields. In the reaction, highly regioselective ring opening of cyclopropane and sequential cyclization occurred. Total synthesis of cyclogalgravin and its dicarboxyl analog was demonstrated by using the SmI2- promoted Reformatsky-type reaction and the Sc(OTf)3-mediated diasteroselective ring expansion as key steps. This method includes a novel transformation of two C-Cl bonds of gem- dichlolocyclopropane to two C-C bonds.
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