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Synthetic study of ent-kaurene diterpenoids based on tandem cyclization reaction

Research Project

Project/Area Number 26460018
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

Suzuki Takahiro  北海道大学, 理学研究院, 准教授 (80367052)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2016: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2015: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2014: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywords有機化学 / 合成化学 / 天然物合成 / ラジカル反応 / 連続反応 / カウレン類 / Diels-Alder反応
Outline of Final Research Achievements

Ent-kaurenes diterpenoids, isolated from isodon herbs such as Rabdosia japonica, are known to have useful biological activities. In this study, we focus on the total synthesis of ent-kauren-15-ones showing NF-κB inhibitory activity. A tandem cyclization reaction was designed as an efficient method for construction of the kaurene skeleton composed of 6/6/6/5 membered rings including bicyclo [3.2.1] octane. As a result of various synthetic investigations, we have found a method based on an intramolecular tandem radical cyclization reaction using low valence titanium ion.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (5 results)

All 2016 2014 Other

All Presentation (3 results) (of which Invited: 2 results) Remarks (2 results)

  • [Presentation] 連続的環化反応を利用したent-カウレン類の合成研究2016

    • Author(s)
      菅野彩夏・鈴木孝洋・谷野圭持
    • Organizer
      第60回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      東京農業大学オホーツクキャンパス(北海道網走市)
    • Year and Date
      2016-10-29
    • Related Report
      2016 Annual Research Report
  • [Presentation] Diels-Alder反応による骨格構築を基盤とした天然物の合成研究2014

    • Author(s)
      鈴木孝洋
    • Organizer
      若手研究者のための有機化学札幌セミナー
    • Place of Presentation
      北海道大学(札幌市)
    • Year and Date
      2014-11-17
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Diels-Alder反応を鍵とする高度に縮環した天然有機化合物の合成研究2014

    • Author(s)
      鈴木孝洋
    • Organizer
      第二回慶應有機化学若手シンポジウム
    • Place of Presentation
      慶応義塾大学日吉キャンパス(横浜市)
    • Year and Date
      2014-05-10
    • Related Report
      2014 Research-status Report
    • Invited
  • [Remarks] 北海道大学理学部化学科 有機化学第二研究室HP

    • URL

      http://barato.sci.hokudai.ac.jp/~oc2/index.html

    • Related Report
      2015 Research-status Report
  • [Remarks] 北海道大学有機化学第二研究室HP

    • URL

      http://barato.sci.hokudai.ac.jp/~oc2/index.html

    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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