A new method for analysis of stereochemistry in carbonyl containing compounds using chemical shifts and spin coupling constant values

• Project/Area Number: 20580118
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Bioproduction chemistry/Bioorganic chemistry
• Research Institution: The Institute of Physical and Chemical Research
• Principal Investigator: KOSHINO Hiroyuki The Institute of Physical and Chemical Research, 物質構造解析チーム, チームヘッド (50321758)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000); Fiscal Year 2010: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2009: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2008: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
• Keywords: CAST / CNMR / 構造訂正 / フォモプシンB / 環状ケトン / テルフェニル / 立体配座 / ケトン / アルデヒド / エステル / ラクトン / スピン結合定数 / テレファンチンG / ロンギフォレン / INADEQUATE法

Research Abstract

Usefulness of geminal spin-coupling constant values on α methylene at carbonyl groups was found and developed as a method for conformational analysis to the dihedral angle between a carbonyl oxygen and methylene protons. To determination of relative stereochemistry through the carbonyl group, comparison of 13C-NMR chemical shift values was effective. Structural revision of phomopsin B was also reported.

Research Products

• [Journal Article] Simple and efficient synthesis of highly functionalized cyclohexanes ; formal total synthesis of ovalicin and fumagillin (2011)
  • Author(s): Shunya Takahashi, Yayoi Hongo, Yue Qi Ye, Hiroyuki Koshino
  • Journal Title: Tetrahedron : Asymmetry 22 Pages: 703-707
  • Peer Reviewed
• [Journal Article] Formal total synthesis of aspergillide A (2011)
  • Author(s): Yuko Izuchi, Nobuhiro Kanomata, Hiroyuki Koshino, Yayoi Hongo, Tadashi Nakata, Shunya Takahashi
  • Journal Title: Tetrahedron : Asymmetry 22 Pages: 246-251
  • Peer Reviewed
• [Journal Article] Structure of formitellan A, a mannofucogalactan from the fruiting Bodies of Fomitella fraxinea (2011)
  • Author(s): S.-M.Cho, B.-S.Yun, I.D.Yoo, H.Koshino
  • Journal Title: Bioorg.Med.Chem.Lett. Volume: 21 Pages: 204-206
  • Peer Reviewed
• [Journal Article] Formal total synthesis of aspergillide A (2011)
  • Author(s): Y.Izuchi, N.Kanomata, H.Koshino, Y.Hongo, T.Nakata, S.Takahashi
  • Journal Title: Tetrahedron : Asymmetry Volume: 22(in press)
  • Peer Reviewed
• [Journal Article] Synthesis of atromentin and its O-alklyated natural products (2010)
  • Author(s): Yue Qi Ye, Hiroyuki Koshino, Naoki Abe, Shunya Takahashi
  • Journal Title: Biosci.Biotechnol.Biochem. 74 Pages: 2342-2344
  • Peer Reviewed
• [Journal Article] A new sesquiterpenoid produced by female Callosobruchus rhodesianus (Pic) : a possible component of the sex attractant pheromone (2010)
  • Author(s): Kenji Shimomura, Hiroyuki Koshino, Arata Yajima, Noriko Matsumoto, Shunsuke Yajima, Kanju Ohsawa
  • Journal Title: Tetrahedron Lett. 51 Pages: 6860-6862
  • Peer Reviewed
• [Journal Article] Studies on natural p-terphenyls : Total syntheses of vialinin A and terrestrin B (2010)
  • Author(s): Yue Qi Ye, Hiroyuki Koshino, Jun-ichi Onose, Kunie Yoshikawa, Naoki Abe, Shunya Takahashi
  • Journal Title: Biosci.Biotechnol.Biochem. 74 Pages: 140-146
  • NAID: 10027550390
  • Peer Reviewed
• [Journal Article] 2,3-Dihydrohomofarnesal : Female sex attractant pheromone component of Callosobruchus rhodesianus (Pic) (2010)
  • Author(s): K.Shimomura, H.Koshino, A.Yajima, N.Matsumoto, Y.Kagohara, K.Kamada, S.Yajima, K.Ohsawa
  • Journal Title: J.Chem.Ecol. Volume: 36 Pages: 824-833
  • Peer Reviewed
• [Journal Article] A new sesquitepenoid produced by female Callosobruchus rhodesianus (Pic) : a possible component of the sex attractant pheromone (2010)
  • Author(s): K.Shimomura, H.Koshino, A.Yajima, N.Matsumoto, S.Yajima, K.Ohsawa
  • Journal Title: Tetrahedron Lett. Volume: 51 Pages: 6860-6862
  • Peer Reviewed
• [Journal Article] Synthesis of atromentin and its O-alkylated natural products (2010)
  • Author(s): Y.Q.Ye, H.Koshino, N.Abe, T.Nakamura, D.Hashizume, S.Takahashi
  • Journal Title: Biosci.Biotechnol.Biochem. Volume: 74 Pages: 2342-2344
  • NAID: 10027561974
  • Peer Reviewed
• [Journal Article] Studies on natural p-terphenyls : total syntheses of vialinin A and terrestrin B (2010)
  • Author(s): Y.Q.Ye, H.Koshino, J.Onose, K.Yoshikawa, N.Abe, S.Takahashi
  • Journal Title: Biosci.Biotechnol.Biochem. 74 Pages: 140-146
  • NAID: 10027550390
  • Peer Reviewed
• [Journal Article] Expeditious synthesis of vialinin B, an extremely potent inhibitor of TNF-α production (2009)
  • Author(s): Yue Qi Ye, Hiroyuki Koshino, Jun-ichi Onose, Kunie Yoshikawa, Naoki Abe, Shunya Takahashi
  • Journal Title: Org.Lett. 11 Pages: 5074-5077
  • Peer Reviewed
• [Journal Article] Structural revision od thelephantin G by total synthesis and the inhibitory activity against TNF-α production (2009)
  • Author(s): Yue Qi Ye, Hiroyuki Koshino, Jun-ichi Onose, Chiemi Negishi, Kunie Yoshikawa, Naoki Abe, Shunya Takahashi
  • Journal Title: J.Org.Chem. 74 Pages: 4642-4645
  • Peer Reviewed
• [Journal Article] Synthesis of all possible isomers corresponding to the proposed structure of montanacin E, and their antitumor activity (2009)
  • Author(s): Shunya Takahashi, Ryotaro Takahashi, Yayoi Hongo, Hiroyuki Koshino, Kazunori Yamaguchi, Taeko Miyagi
  • Journal Title: J.Org.Chem. 74 Pages: 6382-6385
  • Peer Reviewed
• [Journal Article] Synthesis of all possible isomers corresponding to the proposed structure of montanacin E, and their antitumor activity (2009)
  • Author(s): S.Takahashi, R.Takahashi, Y.Hongo, H.Koshino, K.Yamaguchi, T.Miyagi
  • Journal Title: J.Org.Chem. 74 Pages: 6382-6385
  • Peer Reviewed
• [Journal Article] Structural revision of thelephantin G by total synthesis and the inhibitory activity against TNF-α production (2009)
  • Author(s): Y.Q.Ye, H.Koshino, J.Onose, C.Negishi, K.Yoshikawa, N.Abe, S.Takahashi
  • Journal Title: J.Org.Chem. 74 Pages: 4642-4645
  • Peer Reviewed
• [Journal Article] Expeditious synthesis of vialinin B, an extremely potent inhibitor of TNF-α production (2009)
  • Author(s): Y.Q.Ye, H.Koshino, J.Onose, K.Yoshikawa, N.Abe, S.Takahashi
  • Journal Title: Org.Lett. 11 Pages: 5074-5077
  • Peer Reviewed
• [Journal Article] Structure determination of montanacin D by total synthesis (2008)
  • Author(s): Shunya Takahashi, Yayoi Hongo, Yuki Tsukagoshi, Hiroyuki Koshino
  • Journal Title: Org.Lett. 10 Pages: 4223-4226
  • Peer Reviewed
• [Journal Article] Structural determination of montanacin D by total synthesis (2008)
  • Author(s): S. Takahashi, Y. Hongo, Y. Tsukagoshi, H. Koshino
  • Journal Title: Org. Lett. 10 Pages: 4223-4226
  • Peer Reviewed
• [Journal Article] Synthesis and structural revision of phomopsin B, a novel polyketide carrying a 10-membered cyclic-ether ring
  • Author(s): Yuko Izuchi, Hiroyuki Koshino, Yayoi Hongo, Nobuhiro Kanomata, Shunya Takahashi
  • Journal Title: Org.Lett. (in press)
  • Peer Reviewed
• [Presentation] NMRによる構造解析法の開発と構造訂正における合成の重要性 (2010)
  • Author(s): 越野広雪
  • Organizer: 藪田セミナー「天然物有機化合物を起点とした化学生物学の新展開」
  • Place of Presentation: 札幌
  • Year and Date: 2010-06-18
• [Presentation] CAST/CNMRの構造訂正への応用(第4報) (2010)
  • Author(s): 越野広雪,高橋俊哉,佐藤寛子
  • Organizer: 日本農芸化学会2010年度大会
  • Place of Presentation: 東京
  • Year and Date: 2010-03-28
• [Presentation] CAST/CNMRシステムの構造訂正への応用(第4報) (2010)
  • Author(s): 越野広雪、叶躍奇、高橋俊哉、佐藤寛子
  • Organizer: 日本農芸化学会2010年度大会
  • Place of Presentation: (東京大学)東京
  • Year and Date: 2010-03-28
• [Presentation] CAST/CNMRシステムと合成による天然有機化合物の構造訂正 (2009)
  • Author(s): 越野広雪,叶躍奇,高橋俊哉,佐藤寛子
  • Organizer: 第48回NMR討論会
  • Place of Presentation: 福岡
  • Year and Date: 2009-11-10
• [Presentation] CAST/CNMRシステムと合成による天然有機化合物の構造訂正 (2009)
  • Author(s): 越野広雪、叶躍奇、高橋俊哉、佐藤寛子
  • Organizer: 第48回NMR討論会
  • Place of Presentation: (九州大学)福岡
  • Year and Date: 2009-11-10
• [Presentation] CAST/CNMRの構造訂正への応用(第3報) (2009)
  • Author(s): 越野広雪,高橋俊哉,佐藤寛子
  • Organizer: 日本農芸化学会2009年度大会
  • Place of Presentation: 福岡
  • Year and Date: 2009-03-28
• [Presentation] CAST/CNMRシステムの構造訂正への応用(第3報) (2009)
  • Author(s): 越野広雪, 高橋俊哉, 佐藤寛子
  • Organizer: 日本農芸化学会2009年度大会
  • Place of Presentation: 福岡