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Iodocyclization of ynamides

Research Project

Project/Area Number 24590038
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionKobe Pharmaceutical University

Principal Investigator

TAKASHI Okitsu  神戸薬科大学, 薬学部, 講師 (50441209)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2013: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2012: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsイナミド / 環化反応 / ヨウ素 / 複素環
Outline of Final Research Achievements

Ynamides are useful synthons because they exhibit high reactivity toward electrophiles and can be adapted to asymmetric reactions if ynamides are chiral. Therefore, I have developed the iodocyclization of ynamides: for examples, benzofuran synthesis was achieved within three seconds in milder reaction conditions than using normal alkynes. In addition, 6-endo type iodocyclization of homopropargylic hydrazides as substrates proceeded by using ynamides to afford dihydropyridazines. Furthermore, tandem dearomative iodocyclization/ Diels-Alder reaction and polyene cyclization using chiral ynamides were demonstrated in diastereoselective manner to obtain optically active spiro rings and tricyclic skeletons.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (33 results)

All 2015 2014 2013 2012 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results,  Acknowledgement Compliant: 2 results) Presentation (20 results) Remarks (4 results)

  • [Journal Article] Iodocyclization of Ethoxyethyl Ethers to Ynamides: An Immediate Construction to Benzo[b]furans2014

    • Author(s)
      Okitsu, T.; Nakata, K.; Nishigaki, K.; Michioka, N.; Karatani, M.; Wada, A.
    • Journal Title

      J. Org. Chem.

      Volume: 79 Issue: 12 Pages: 5914-5920

    • DOI

      10.1021/jo500903y

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Color Discriminating Retinal Configurations of Sensory Rhodopsin I by Photo-Irradiation Solid State NMR Spectroscopy.2014

    • Author(s)
      H. Yomonda, Y. Makino, Y. Tomonaga, T. Hidaka, I. Kawamura*, T. Okitsu, A. Wada, Y. Sudo*, A. Naito*.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 53 Issue: 27 Pages: 6960-6964

    • DOI

      10.1002/anie.201309258

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Inhibition of lysine-specific demethylase 1 by the acyclic diterpenoid geranylgeranoic acid and its derivatives.2014

    • Author(s)
      Sakane C, Okitsu T, Wada A, Sagami H, Shidoji Y.
    • Journal Title

      Biochem Biophys Res Commun.

      Volume: 444 Issue: 1 Pages: 24-29

    • DOI

      10.1016/j.bbrc.2013.12.144

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Solid-state NMR 13C and 15N resonance assignments of a seven-transmembrane helical protein Anabaena Sensory Rhodopsin2013

    • Author(s)
      Wang, S.; Shi, L.; Okitsu, T.; Wada, A.; Brown, L. S.; Ladizhansky, V.
    • Journal Title

      Biomol. NMR Assign.

      Volume: 7(2) Issue: 2 Pages: 253-265

    • DOI

      10.1007/s12104-012-9421-y

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Solid-state NMR spectroscopy structure determination of a lipid-embedded heptahelical membrane protein2013

    • Author(s)
      Wang, S.; Munro, R. A.; Shi, L.; Kawamura, I.; Okitsu, T.; Wada, A.; Kim, S.-Y.; Jung, K.-H.; Brown, L. S.; Ladizhansky, V.
    • Journal Title

      Nature Methods

      Volume: 10(10) Issue: 10 Pages: 1007-1012

    • DOI

      10.1038/nmeth.2635

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Menadione (vitamin K_3) is a catabolic product of oral phylloquin one (vitamin K1) in the intestine and a circulating precursor of tissue menaquinone-4 (vitamin K_2) in rats.2013

    • Author(s)
      Yoshihisa Hirota
    • Journal Title

      The Journal of Biological Chemistry

      Volume: 288 Issue: 46 Pages: 33071-33080

    • DOI

      10.1074/jbc.m113.477356

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Substituent effect of bis(pyrimidines)iodonium complexes as iodinating reagent: Control of the iodocyclization/oxidation process2013

    • Author(s)
      Okitsu, T.; Yumitate, S.; Sato, K.; In, Y.; Wada, A.
    • Journal Title

      Chem. Eur. J.

      Volume: 19(16) Issue: 16 Pages: 4992-4996

    • DOI

      10.1002/chem.201204423

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Large spectral change due to amide modes of a β-sheet upon the formation of an early photointermediate of middle rhodopsin2013

    • Author(s)
      Furutani, Y., Okitsu, T., Reissig, L., Mizuno, M., Homma, M., Wada, A., Mizutani, Y., Sudo, Y.
    • Journal Title

      J. Phys. Chem. B

      Volume: 117 Issue: 13 Pages: 3449-3458

    • DOI

      10.1021/jp308765t

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Correlation between nuptial colors and visual sensitivities tuned by opsins leads to species richness in sympatric Lake Victoria cichlid fishes2012

    • Author(s)
      Miyagi R, Terai Y, Aibara M, Sugawara T, Imai H, Tachida H, Mzighani SI, Okitsu T, Wada A, Okada N
    • Journal Title

      Mol Biol Evol

      Volume: 29 Issue: 11 Pages: 3281-96

    • DOI

      10.1093/molbev/mss139

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] 3-メチレン-4-アミド-1,2-ジアゼチジンの求核的開環反応におけるアレナミドの基質一般性の検討2015

    • Author(s)
      沖津 貴志、菅 凌介、松井 佑記、和田 昭盛
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
  • [Presentation] 3-メチレン-4-アミド-1,2-ジアゼチジンの求核的開環反応2014

    • Author(s)
      沖津 貴志、小林 恵子、吉田 淳美、吉田 裕司、和田 昭盛
    • Organizer
      第40回反応と合成の進歩シンポジウム
    • Place of Presentation
      仙台
    • Year and Date
      2014-11-10
    • Related Report
      2014 Annual Research Report
  • [Presentation] Preparation of Red-Shifted PSB of Retinal Having Enamine Structure2014

    • Author(s)
      Wada, A.; Okitsu, T.; Futamura, N.; Niimi, Y.; Ishizuka, T.; Yawo, H.; Matsuyama Hoyos, T.; Yamashiya, T.; Shichida, Y.
    • Organizer
      16th International Conference on Retinal Proteins
    • Place of Presentation
      Nagahama
    • Year and Date
      2014-10-05 – 2014-10-10
    • Related Report
      2014 Annual Research Report
  • [Presentation] イナミドのヨード環化反応を利用したベンゾフランの即時合成2014

    • Author(s)
      沖津 貴志、中田 康平、西垣 賢志、道岡 直幸、柄谷 光章、和田 昭盛
    • Organizer
      第17回ヨウ素学会シンポジウム
    • Place of Presentation
      千葉
    • Year and Date
      2014-09-19
    • Related Report
      2014 Annual Research Report
  • [Presentation] 3-メチレン-4-アミド-1,2-ジアゼチジンへのアリルシランの求核的開環反応2014

    • Author(s)
      沖津 貴志、小林 恵子、吉田 淳美、和田 昭盛
    • Organizer
      第34回有機合成若手セミナー
    • Place of Presentation
      神戸
    • Year and Date
      2014-08-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] Substitution effect of bis(pyridines)iodonium complexes as iodinating reagents2013

    • Author(s)
      Okitsu, T.; Yumitate, S.; Sato, K.; In, Y.; Wada, A.
    • Organizer
      14th Tetrahedron Symposium
    • Place of Presentation
      Vienna
    • Related Report
      2013 Research-status Report
  • [Presentation] 11-シス-デメチルレチノイン酸類の効率的合成とその生物活性

    • Author(s)
      辻本 麻里、近野 沙織、沖津 貴志、松浦 直美、中川 公恵、岡野 登志夫、和田 昭盛
    • Organizer
      日本ビタミン学会第65回大会
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
  • [Presentation] メントン由来二環性骨格を有する9-cis-レチノイン酸誘導体の合成とRXRアゴニスト活性

    • Author(s)
      沖津 貴志、山田 翔也、加来田 博貴、和田 昭盛
    • Organizer
      日本レチノイド研究会第24回学術集会
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
  • [Presentation] ヨウ素試薬を用いたイナミドのポリエン環化反応の開発

    • Author(s)
      沖津 貴志、向井 美好、和田 昭盛
    • Organizer
      第63回日本薬学会近畿支部総会・大会
    • Place of Presentation
      京田辺
    • Related Report
      2013 Research-status Report
  • [Presentation] イナミドの特性を生かしたヨード環化反応の開発

    • Author(s)
      沖津 貴志、中田 康平、村井 ちはる、和田 昭盛
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      福岡
    • Related Report
      2013 Research-status Report
  • [Presentation] 長波長ロドプシン作製を指向した共役系伸長レチナール類の合成

    • Author(s)
      沖津 貴志、小林 由佳、和田 昭盛
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本
    • Related Report
      2013 Research-status Report
  • [Presentation] アレナミド、アゾ化合物、アリルシランの三成分カップリング

    • Author(s)
      沖津 貴志、吉田 淳美、小林 恵子、和田 昭盛
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本
    • Related Report
      2013 Research-status Report
  • [Presentation] イナミドのヨード環化反応を利用したピリダジン類の合成

    • Author(s)
      沖津 貴志、森澤 祐介、和田 昭盛
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本
    • Related Report
      2013 Research-status Report
  • [Presentation] 遠隔不斉誘起型ヨード環化反応-光学活性なスピロ化合物の合成-

    • Author(s)
      沖津 貴志、村井 ちはる、和田 昭盛
    • Organizer
      第62回日本薬学会近畿支部総会・大会
    • Place of Presentation
      西宮
    • Related Report
      2012 Research-status Report
  • [Presentation] 9Z-デメチルレチノイン酸類の効率的合成とその生物活性

    • Author(s)
      和田 昭盛、沖津 貴志、近野 沙織、辻本 麻里、松浦 直美、中川 公恵、岡野 登志夫
    • Organizer
      第56回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      鹿児島
    • Related Report
      2012 Research-status Report
  • [Presentation] 酸-塩基複合系を利用したイソシアニドのカルボアルコキシ化

    • Author(s)
      沖津 貴志、長瀬 建太、西尾 信彦、和田 昭盛
    • Organizer
      第38回反応と合成の進歩シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2012 Research-status Report
  • [Presentation] Synthesis of Benzoxazoles by Tandem Migration-Carboalkoxylation

    • Author(s)
      Okitsu, T.; Nagase, K.; Nishio, N.; Wada, A.
    • Organizer
      IKCOC-12
    • Place of Presentation
      Kyoto
    • Related Report
      2012 Research-status Report
  • [Presentation] メントン由来の二環性骨格を有する9-cis-レチノイン酸誘導体型RXRアゴニストの創製

    • Author(s)
      沖津 貴志、山田 翔也、加来田 博貴、和田 昭盛
    • Organizer
      第30回メディシナルケミストリーシンポジウム
    • Place of Presentation
      東京
    • Related Report
      2012 Research-status Report
  • [Presentation] イナミドのヨード環化反応を利用したベンゾフランの迅速合成

    • Author(s)
      沖津 貴志、中田 康平、和田 昭盛
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      東京
    • Related Report
      2012 Research-status Report
  • [Presentation] アレナミドとアゾ化合物の[2 + 2]環化付加反応と続く求核的開環反応の開発

    • Author(s)
      沖津 貴志、吉田 裕司、和田 昭盛
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      東京
    • Related Report
      2012 Research-status Report
  • [Remarks] 神戸薬科大学・生命有機化学研究室

    • URL

      http://www.kobepharma-u.ac.jp/ocls/

    • Related Report
      2014 Annual Research Report
  • [Remarks] 神戸薬科大学・学術活動一覧

    • URL

      http://www.kobepharma-u.ac.jp/guid/guid_09d.html

    • Related Report
      2013 Research-status Report
  • [Remarks] 神戸薬科大学・生命有機化学研究室

    • URL

      http://www.kobepharma-u.ac.jp/~ocls/

    • Related Report
      2013 Research-status Report
  • [Remarks] 神戸薬科大学 生命有機化学研究室

    • URL

      http://www.kobepharma-u.ac.jp/~ocls/

    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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