Synthetic Studies of Natural Products Containing an Eight-Membered Ring Featuring Tandem Carbon-Carbon Bond Formation.

• Project/Area Number: 20790011
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: Hiroshima University
• Principal Investigator: SASAKI Michiko Hiroshima University, 医歯薬学総合研究科, 助教 (30379888)
• Project Period (FY): 2008 – 2009
• Project Status: Completed (Fiscal Year 2009)
• Budget Amount: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000); Fiscal Year 2009: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2008: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: 合成化学 / 全合成 / 「3+4」アニュレーション / 八員環化合物

Research Abstract

A Brook rearrangement-mediated [3+4] annulation was applied to the synthesis of some natural products containing eight-membered ring system. We have accomplished the synthesis of the core of asteriscanolide and the formal syntheses of (+)-laurallene and (+)-prelaureatin.

Research Products

• [Journal Article] Stereoselective Brook Rearrangement-Mediated SE2' Protonation of a-Hydroxy Allyl Silanes (2009)
  • Author(s): Michiko Sasaki, Yuri Shirakawa, Masatoshi Kawahata, Kentaro Yamaguchi, Kei Takeda
  • Journal Title: Chem. Eur. J 15 Pages: 3363-3366
  • Peer Reviewed
• [Journal Article] [2,3]-Wittig Rearrangement of Enantiomerically Enriched 3-Substituted 1-Propenyl oxy-1-phenyl-2-propen-1-yl Carbanions : Effect of Heteroatoms and Conjugating Groups on Planarization of an a-Oxy-Benzylcarbanion Through a Double Bond (2009)
  • Author(s): Michiko Sasaki
  • Journal Title: Chemistry-A European Journal 15 Pages: 4663-4666
  • Peer Reviewed
• [Journal Article] Development of Epoxysilane Rearrangement and its Application to Chirality Transfer (2009)
  • Author(s): Michiko Sasaki
  • Journal Title: Heterocycles 78 Pages: 2919-2941
  • NAID: 40016842003
  • Peer Reviewed
• [Journal Article] Stereoselective Brook Rearrangement-Mediated S_E2' Protonation of α-Hydroxy Allyl Silanes (2009)
  • Author(s): Michiko Sasaki
  • Journal Title: Chemistry-A European Journal Pages: 3363-3366
  • Peer Reviewed
• [Journal Article] Diastereoselective Brook Rearrangement-Mediated [3 + 4] Annulation: Application to a Formal Synthesis of (+)-Laurallene (2008)
  • Author(s): Michiko Sasaki, Azusa Hashimoto, Koudai Tanaka, Masatoshi Kawahata, Kentaro Yamaguchi, Kei Takeda
  • Journal Title: Org. Lett 10 Pages: 1803-1806
  • Peer Reviewed
• [Journal Article] Diastereoselective Brook Rearrangement-Mediated [3+4] Annulation : Application to a Formal Synthesis of (+)-Laurallene (2008)
  • Author(s): Michiko Sasaki
  • Journal Title: Organic Letters 10 Pages: 1803-1806
  • Peer Reviewed
• [Journal Article] Chirality Transfer from Epoxide to Carbanion : Base-Induced Alkylation of O-Carbamoyl Cyanohydrins of β-Silyl-α, β-epoxyaldehyde (2008)
  • Author(s): Michiko Sasaki
  • Journal Title: European Journal of Organic Chemistry Pages: 3061-3064
  • Peer Reviewed
• [Presentation] Brook転位を利用するシロキシアレンのエナンチオ選択的合成法の開発 (2010)
  • Author(s): 佐々木道子
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山市
  • Year and Date: 2010-03-29
• [Presentation] キラルカルバニオンの立体化学的安定性に対する溶媒効果 (2010)
  • Author(s): 佐々木道子
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山市
  • Year and Date: 2010-03-29
• [Presentation] [3+4]アニュレーションを用いる(+)-Prelaureatinの合成研究 (2009)
  • Author(s): 佐々木道子
  • Organizer: 第35回反応と合成の進歩シンポジウム
  • Place of Presentation: 金沢市
  • Year and Date: 2009-11-17
• [Presentation] Effects of Solvents on the Trapping of Chiral Carbanions by [2,3]-Wittig Rearrangement (2009)
  • Author(s): Michiko Sasaki
  • Organizer: 11th International Kyoto Conference on New Aspects of Organic Chemistry
  • Place of Presentation: 京都市
  • Year and Date: 2009-11-10
• [Presentation] [3+4]アニュレーションを利用する(+)-Prelaureatinの合成研究 (2009)
  • Author(s): 佐妹道子
  • Organizer: 第48回日本薬学会・日本病院薬剤師会中国四国支部学術大会
  • Place of Presentation: 徳島市
  • Year and Date: 2009-11-07
• [Presentation] Brook転位を利用する光学活性シロキシアレンの合成 (2009)
  • Author(s): 佐々木道子
  • Organizer: 第48回日本薬学会・日本病院薬剤師会中国四国支部学術大会
  • Place of Presentation: 徳島市
  • Year and Date: 2009-11-07
• [Presentation] [2,3]-Wittig転位を利用するキラルカルバニオンの立体化学的安定性の評価 (2009)
  • Author(s): 佐々木道子
  • Organizer: 第7回次世代を担う有機化学シンポジウム
  • Place of Presentation: 大阪市
  • Year and Date: 2009-07-23
• [Presentation] Use of a Brook Rearrangement- Mediated [3 + 4] Annulation Toward the Total Synthesis of (+)-Prelaureatin (2009)
  • Author(s): Michiko Sasaki, Kazuhisa Oyamada, Kei Takeda
  • Organizer: 41st National Organic Chemistry Symposium
  • Place of Presentation: Boulder, CO, USA
  • Year and Date: 2009-06-08
• [Presentation] Use of a Brook Rearrangement-Mediated [3+4] Annulation Toward the Total Synthesis of (+)-Prelaureatin (2009)
  • Author(s): Michiko Sasaki
  • Organizer: 41st National Organic Chemistry Symposium
  • Place of Presentation: Boulder, CO, USA
  • Year and Date: 2009-06-08
• [Presentation] Trapping of Chiral Carbanions by [2,3]-Wittig Rearrangement : Effect of Heteroatoms and Conjugating Groups (2009)
  • Author(s): Michiko Sasaki
  • Organizer: 41st National Organic Chemistry Symposium
  • Place of Presentation: Boulder, CO, USA
  • Year and Date: 2009-06-08
• [Presentation] 光学活性α-ヒドロキシアリルシランのS_E2'型反応を利用する不斉転写 (2009)
  • Author(s): 佐々木道子
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都市
  • Year and Date: 2009-03-26
• [Presentation] [2, 3]-Wittig転位を利用するキラルカルバニオンの立体化学的安定性の評価 (2009)
  • Author(s): 佐々木道子
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都市
  • Year and Date: 2009-03-26
• [Presentation] [3+4]アニュレーションを用いる(+)-Prelaureatinの合成研究 (2008)
  • Author(s): 佐々木道子
  • Organizer: 第38回複素環化学討論会
  • Place of Presentation: 福山市
  • Year and Date: 2008-11-22
• [Presentation] [2, 3]-Wittig転位を利用するキラルヵルバニォンの立体化学的安定性の比較 (2008)
  • Author(s): 佐々木道子
  • Organizer: 第34回反応と合成の進歩シンポジウム
  • Place of Presentation: 京都市
  • Year and Date: 2008-11-04
• [Presentation] Trapping of Chiral Carbanions by [2, 3]-Wittig Rearrangement (2008)
  • Author(s): Michiko Sasaki
  • Organizer: The 236th National Meeting of the American Chemical Society
  • Place of Presentation: Philadelphia, PA, USA
  • Year and Date: 2008-08-19
• [Presentation] Chirality Transfer from Epoxide to Carbanion : Base-induced Alkylation of O-Carbamoyl Cyanohydrins of β-Silyl-α, β-epoxyaldehyde (2008)
  • Author(s): Michiko Sasaki
  • Organizer: The 236th National Meeting of the American Chemical Society
  • Place of Presentation: Philadelphia, PA, USA
  • Year and Date: 2008-08-19
• [Presentation] Trapping of Chiral Carbanions by [2, 3]-Wittig Rearrangement (2008)
  • Author(s): Michiko Sasaki, Hidaka Ikemoto, Mariko Higashi, Kei Takeda
  • Organizer: The 236th National Meeting of the American Chemical Society (Sci-Mix)
  • Place of Presentation: Philadelphia, PA, USA
  • Year and Date: 2008-08-18
• [Remarks]
  • URL: http://home.hiroshima-u.ac.jp/takedake/
• [Remarks]
  • URL: http://home.hiroshima-u.ac.jp/takedake/index-e.html
• [Remarks]
  • URL: http://home.hiroshima-u.ac.jp/takedake/
• [Remarks]
  • URL: http://home.hiroshima-u.ac.jp/takedake/