2015 Fiscal Year Final Research Report
Stereocontrolled synthesis of functionalized biaryl derivatives possessing axial chirality and stereogenic center(s)
| Project/Area Number |
25460024
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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 |
Chemical pharmacy
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| Research Institution | Tokyo University of Pharmacy and Life Science |
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Principal Investigator |
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| Project Period (FY) |
2013-04-01 – 2016-03-31
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| Keywords | 有機化学 / 合成化学 / 生物活性天然物 |
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| Outline of Final Research Achievements |
Two novel methods have been developed for the stereocontrolled synthesis of functionalized biaryl derivatives possessing both axial chirality and central chirality: (1) One utilizes enantioselective desymmetrization of achiral biphenyl-2,6-diyl diacetate derivatives through the lipase-catalyzed mono-hydrolysis for the control of axial stereochemistry. The subsequent diastereoselective construction of a stereogenic center on the side chain portion and the formation of the eight-membered carbocyclic bridge by ring-closing metathesis offers an efficient entry to the optically active dibenzocyclooctadiene core of gomicin/schsandrine-type lignans. The other method utilizes diastereoselective desymmetrization through the medium-sized lactone formation of a biphenyl-2,6-diol, which possesses, at the C2' position, an alkanoic-acid side chain containing a stereogenic center, enabling highly stereoselective access to a series of 8-10-membered lactone-annulated biphenyls.
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| Free Research Field |
医歯薬学
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