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2012 Fiscal Year Final Research Report

Synthetic study of highly oxygenated diterpenes based on the bridgehead radical reaction

Research Project

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Project/Area Number 23790005
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionThe University of Tokyo

Principal Investigator

URABE Daisuke  東京大学, 大学院・薬学系研究科, 助教 (80503515)

Project Period (FY) 2011 – 2012
Keywords全合成 / ラジカル反応 / 天然物 / 生理活性物質 / テルペン
Research Abstract

The C-C bond formation utilizing an alkoxy bridgehead carbon radical was developed. The high reactivity of the radical species realized the congested C-C bond formation to connect oxygenated carbocycles by two- and three-component reactions. Based on the strategy, the5/7/6-fused carbocycles of crotophorbolone, a tigliane diterpene, was successfully assembled in a stereoselective fashion.

  • Research Products

    (35 results)

All 2013 2012 2011 Other

All Journal Article (13 results) (of which Peer Reviewed: 12 results) Presentation (20 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results) (of which Overseas: 1 results)

  • [Journal Article] Preparation and palladium-mediated cross-coupling of --benzoyloxyalkylzinc bromides2013

    • Author(s)
      Sakata, K.; Urabe, D.; Inoue, M
    • Journal Title

      Tetrahedron Letters

      Volume: (in press)

    • DOI

      DOI:10.1016/j.tetlet.2013.05.114

    • Peer Reviewed
  • [Journal Article] A convergent total synthesis of19-hydroxysarmentogenin.2013

    • Author(s)
      Mukai, K.; Urabe, D.; Kasuya, S.; Aoki, N.; Inoue, M
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 52 Pages: 5300-5304

    • DOI

      DOI:10.1002/anie.201302067

    • Peer Reviewed
  • [Journal Article] A radical-based approach for the construction of the tetracyclic structure of resiniferatoxin2013

    • Author(s)
      Murai, K.; Katoh, S.; Urabe, D.; Inoue, M
    • Journal Title

      Chemical Science

      Volume: 4 Pages: 2364-2368

    • DOI

      DOI:10.1039/C3SC50329A

    • Peer Reviewed
  • [Journal Article] Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative2013

    • Author(s)
      Tabuchi, T.; Urabe, D.; Inoue, M
    • Journal Title

      Beilstein Journal of Organic Chemistry

      Volume: 9 Pages: 655-663

    • DOI

      DOI:10.3762/bjoc.9.74

    • Peer Reviewed
  • [Journal Article] Symmetry-driven synthesis of9-demethyl-10,15-dideoxyryanodol2013

    • Author(s)
      Urabe, D.; Nagatomo, M.; Hagiwara, K.;Masuda, K.; Inoue, M
    • Journal Title

      Chemical Science

      Volume: 4 Pages: 1615-1619

    • DOI

      DOI:10.1039/C3SC00023K

    • Peer Reviewed
  • [Journal Article] Selective introduction of four contiguous stereocenters on the B-ring of4-hydroxyzinowol2012

    • Author(s)
      Iwatsu, M.; Urabe, D.; Todoroki, H.; Masuda, K.; Inoue, M
    • Journal Title

      Heterocycles

      Volume: 86 Pages: 181-188

    • DOI

      DOI:10.3987/COM-12-S(N)76

    • Peer Reviewed
  • [Journal Article] Intermolecular radical reaction of O,Se-acetals generated via seleno-Pummererrear rangement2012

    • Author(s)
      Urabe, D.; Yamaguchi, H.; Someya, A.Inoue, M
    • Journal Title

      Organic Letters

      Volume: 14 Pages: 3842-3845

    • DOI

      DOI:10.1021/ol301482f

    • Peer Reviewed
  • [Journal Article] Total syntheses of four possible stereoisomers of resolvin E32012

    • Author(s)
      Urabe, D.; Todoroki, H.; Masuda, K.; Inoue, M
    • Journal Title

      Tetrahedron

      Volume: 68 Pages: 3210-3219

    • DOI

      DOI:10.1016/j.tet.2012.02.04510

    • Peer Reviewed
  • [Journal Article] Identification of and structure determination of a novel anti-inflammatory mediator resolvin E32012

    • Author(s)
      Isobe, Y.; Arita, M.; Matsueda, S.; Iwamoto, R.; Fujiwara, T.; Nakanishi, H.; Taguchi, R.; Masuda, K.; Sasaki, K.; Urabe, D.; Inoue, M.; Arai, H
    • Journal Title

      The Journal of Biological Chemistry

      Volume: 287 Pages: 10525-10534

    • DOI

      DOI:10.1074/jbc.M112.340612

    • Peer Reviewed
  • [Journal Article] Total synthesis and bioactivities of two proposed structures of maresin2011

    • Author(s)
      Sasaki, K.; Urabe, D.; Arai, H.; Arita, M.; Inoue, M
    • Journal Title

      Chemistry-An Asian Journal

      Volume: 6 Pages: 534-543

    • DOI

      DOI:10.1002/asia.201000494

    • Peer Reviewed
  • [Journal Article] Application of --alkoxy bridgehead radical for coupling of oxygenated carbocycles2011

    • Author(s)
      Urabe, D.; Yamaguchi, H.; Inoue, M
    • Journal Title

      Organic Letters

      Volume: 13 Pages: 4778-4781

    • DOI

      DOI:10.1021/ol201758a

    • Peer Reviewed
  • [Journal Article] ラジカル反応を機軸とする複雑天然物の合成2011

    • Author(s)
      井上将行、占部大介
    • Journal Title

      化学工業

      Volume: 62 Pages: 594-596

  • [Journal Article] Stereochemical assignment and anti-inflammatory properties of the omega-3 lipid mediator resolvin E3

    • Author(s)
      Isobe, Y.; Arita, M.; Iwamoto, R.; Urabe, D.; Todoroki, H.; Masuda, K.; Inoue, M.; Arai, H
    • Journal Title

      The Journal of Biochemistry

      Volume: 153 Pages: 355-360

    • DOI

      DOI:10.1093/jb/mvs151

    • Peer Reviewed
  • [Presentation] クロトホルボロンの全合成研究2013

    • Author(s)
      浅羽太郎、占部大介、井上将行
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Year and Date
      20130327-30
  • [Presentation] レジニフェラトキシンの合成研究2013

    • Author(s)
      加藤駿一郎、村井耕一、占部大介、井上将行
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Year and Date
      20130327-30
  • [Presentation] トウセンダニンの合成研究2013

    • Author(s)
      福島圭一郎、青木直人、占部大介、井上将行
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Year and Date
      20130327-30
  • [Presentation] α-アシルオキシ有機亜鉛化合物によるクロスカップリング反応の開発2013

    • Author(s)
      坂田光命、占部大介、井上将行
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Year and Date
      20130327-30
  • [Presentation] レイサンチンBの合成研究2013

    • Author(s)
      轟木秀憲、枡田健吾、占部大介、井上将行
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Year and Date
      20130327-30
  • [Presentation] Study Toward Total Synthesis of Ryanodine2012

    • Author(s)
      Nagatomo, M.; Hagiwara, K.; Tabuchi, T.; Urabe, D.; Inoue, M. A
    • Organizer
      AIMECS11
    • Place of Presentation
      Tokyo
    • Year and Date
      20121130-1202
  • [Presentation] Study towards the Total Synthesis of Resiniferatoxin2012

    • Author(s)
      Murai, K.; Katoh, S.; Urabe, D.; Inoue, M
    • Organizer
      IKCOC-12
    • Place of Presentation
      Kyoto
    • Year and Date
      20121112-16
  • [Presentation] 19-ヒドロキシサルメントゲニンの全合成2012

    • Author(s)
      向井健、粕谷智史、青木直人、占部大介、井上将行
    • Organizer
      第54回天然有機化合物討論会
    • Place of Presentation
      東京
    • Year and Date
      20120918-20
  • [Presentation] Synthetic study of talatisamine2012

    • Author(s)
      Tabiuchi, T.; Urabe, D.; Inoue, M
    • Organizer
      The 6th Takeda Science Foundation Symposium on PharmaSciences
    • Place of Presentation
      Osaka
    • Year and Date
      20120913-14
  • [Presentation] -オキシ炭素ラジカルを用いた分子間C-C結合形成反応の開発2012

    • Author(s)
      占部大介、山口裕樹、染谷あゆみ、井上将行
    • Organizer
      第101回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      20120606-07
  • [Presentation] タラチサミンの全合成研究2012

    • Author(s)
      田渕俊樹、占部大介、井上将行
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      20120328-31
  • [Presentation] アルコキシ橋頭位ラジカルを用いた高酸化度炭素環の効率的連結2012

    • Author(s)
      山口裕樹、占部大介、井上将行
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      20120328-31
  • [Presentation] リアノジンの不斉合成研究2012

    • Author(s)
      枡田健吾、長友優典、占部大介、井上将行
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      20120328-31
  • [Presentation] クロトホルボロンの合成研究2012

    • Author(s)
      浅羽太郎、嘉藤裕樹、占部大介、井上将行
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      20120328-31
  • [Presentation] Synthetic study of hyponine B2012

    • Author(s)
      Ishiyama, T.; Urabe, D.; Inoue, M
    • Organizer
      IKCOC-12
    • Place of Presentation
      Kyoto
    • Year and Date
      2012-11-11
  • [Presentation] レジニフェラトキシンの合成研究2012

    • Author(s)
      加藤駿一郎、村井耕一、占部大介、井上将行
    • Organizer
      第56回日本薬学会関東支部大会
    • Place of Presentation
      東京
    • Year and Date
      2012-10-13
  • [Presentation] レジニフェラトキシンの全合成研究2012

    • Author(s)
      村井耕一、加藤駿一郎、占部大介、井上将行
    • Organizer
      第10回次世代を担う有機化学シンポジウム
    • Place of Presentation
      大阪
    • Year and Date
      2012-05-11
  • [Presentation] Synthetic study of resiniferatoxin2011

    • Author(s)
      Murai, K.; Urabe, D.; Inoue, M
    • Organizer
      AIMECS11
    • Place of Presentation
      Tokyo
    • Year and Date
      20111130-1202
  • [Presentation] Synthetic study of hyponine B2011

    • Author(s)
      Ishiyama, T.; Urabe, D.; Inoue, M
    • Organizer
      AIMECS11
    • Place of Presentation
      Tokyo
    • Year and Date
      20111130-1202
  • [Presentation] レゾルビンE3の全合成2011

    • Author(s)
      轟木秀憲、増田功嗣、占部大介、井上将行
    • Organizer
      第99回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      20110615-16
  • [Remarks]

    • URL

      http://www.f.u-tokyo.ac.jp/~inoue/

  • [Patent(Industrial Property Rights)] 光学活性な新規抗炎症性化合物およびその製造方法2011

    • Inventor(s)
      有田誠、井上将行、占部大介、新井 洋由、増田功嗣
    • Industrial Property Rights Holder
      東京大学
    • Industrial Property Number
      特許権,2011-017166
    • Filing Date
      2011-01-28
    • Overseas

URL: 

Published: 2014-09-25  

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