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 |
Section | 一般 |
Research Field |
Chemical pharmacy
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Research Institution | Tokyo University of Pharmacy and Life Science |
Principal Investigator |
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Project Period (FY) |
2013-04-01 – 2016-03-31
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Project Status |
Completed (Fiscal Year 2015)
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Budget Amount *help |
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2015: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2013: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
|
Keywords | 有機化学 / 合成化学 / 生物活性天然物 / 天然物合成 / 立体制御反応 / 軸不斉 |
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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Report
(4 results)
Research Products
(31 results)
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[Presentation] 置換ジベンゾシクロオクタジエンの立体選択的合成法2016
Author(s)
Daisuke Yanagisawa, Asami Inoue, Kayo Sakamoto, Satoru Yamaguchi, Hikaru Yanai, Keisuke Suzuki, Takashi Matsumoto
Organizer
日本薬学会 第136年会
Place of Presentation
横浜
Year and Date
2016-03-26
Related Report
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[Presentation] ラクトン架橋の形成を利用した軸不斉ビフェニルの立体選択的合成法2016
Author(s)
Erina Tsuruta, Daisuke Yuyama, Nanami Sugiyama, Satoru Yamaguchi, Hikaru Yanai, Keisuke Suzuki, Takashi Matsumoto
Organizer
日本薬学会 第136年会
Place of Presentation
横浜
Year and Date
2016-03-26
Related Report
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[Presentation] フルオロベンゼン誘導体を活用する置換キサントンの効率的合成法2015
Author(s)
Yuuki Fujimoto, Ryohei Itakura, Hiroki Hoshi, Haruhito Kurokawa, Hiromi Ito, Yumina Ito, Yu Watabe, Yosio Ando, Keisuke Suzuki, Yasuo Dabashi, Hikaru Yanai, Takashi Matsumoto
Organizer
第107 回有機合成シンポジウム
Place of Presentation
東京
Year and Date
2015-06-09
Related Report
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