Synthetic studies of nitrogen-containing natural products with unique structures

• Project/Area Number: 17310129
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Living organism molecular science
• Research Institution: Kochi University
• Principal Investigator: ICHIKAWA Yoshiyasu Kochi University, 教育研究部自然科学系, 教授 (60193439)
• Co-Investigator(Kenkyū-buntansha): KOTSUKI Hiyoshizo 高知大学, 教育研究部自然科学系, 教授 (80093954) ; NAKANO Keijo 高知大学, 教育研究部自然科学系, 講師 (50399747)
• Project Period (FY): 2005 – 2008
• Project Status: Completed (Fiscal Year 2008)
• Budget Amount: ¥16,530,000 (Direct Cost: ¥15,300,000、Indirect Cost: ¥1,230,000); Fiscal Year 2008: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000); Fiscal Year 2007: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000); Fiscal Year 2006: ¥2,400,000 (Direct Cost: ¥2,400,000); Fiscal Year 2005: ¥8,800,000 (Direct Cost: ¥8,800,000)
• Keywords: 天然物化学 / 生物有機化学 / 有機合成化学 / 含窒素化合物 / 転位反応 / 糖化学 / 生体機能分子 / 抗生物質 / 有機化学 / グリコシル化反応 / アミノ糖 / シグマトロピー反応 / イソシアナート / 合成化学 / イソニトリル

Research Abstract

特異な構造をもつ含窒素天然物の合成研究を行った。含窒素天然物として,異常アミノ酸であるα, β-ジアミノ酸,海洋天然物アゲラスタチンAとパチャストリサミン,アミノ糖系抗生物質グリコシンナスペリミシンDを標的化合物として選んだ。アリルシアナートの転位反応を基軸として研究を推進して, 従来法に比べ効率的な合成ルートの開拓に成功した。

Research Products

• [Journal Article] Stereocontrolled synthesis of cytotoxic anhydrosphingosine pachastrissamine by using [3.3] sigmatropic rearrangement of allyl cyanate (2008)
  • Author(s): Ichikawa, Y. ; Matsunaga, K. ; Masuda, T. ; Kotsuki, H. ; Nakano, K.
  • Journal Title: Tetrahedron 64 Pages: 11313-11318
  • Peer Reviewed
• [Journal Article] Microwave-Assisted and Ln(OTf)_3-Catalyzed Homo-conjugate Addition of N-Heteroaromatics to Activated Cyclopropane Derivatives (2008)
  • Author(s): Uddin, M-I. ; Mimoto, A. ; Nakano, K. ; Ichikawa, Y. ; Kotsuki, H,
  • Journal Title: Tetrahedron Lett. 49 Pages: 5867-5870
  • Peer Reviewed
• [Journal Article] A Novel Method for the High-Pressure-Promoted, Uncatalyzed Aza-Michael Reaction of Nitrogen Heterocycles with Enones in Water (2008)
  • Author(s): Uddin, M-I. ; Nakano, K. ; Ichikawa, Y. ; Kotsuki, H.
  • Journal Title: Synlett Pages: 1402-1406
  • NAID: 120001548987
  • Peer Reviewed
• [Journal Article] Stereocontrolled synthesis of cytotoxic anhydrosphingosine pachastrissamine by using[3.3] sigmatropic rearrangement of allyl cyanate (2008)
  • Author(s): Ichikawa, Y., Matsunaga, K., Masuda, T., Kotsuki, H., Nakano, K
  • Journal Title: Tetrahedron 64 Pages: 11313-11318
  • Peer Reviewed
• [Journal Article] A Novel Method for the High-Pressure-Promoted, Uncatalyzed Aza-Michael Reaction of Nitrogen Heterocycles with Enones in Water. (2008)
  • Author(s): Uddin, M-I., Nakano, K, Ichikawa, Y., Kotsuki, H
  • Journal Title: Synlett なし Pages: 1402-1406
  • NAID: 120001548987
  • Peer Reviewed
• [Journal Article] Microwave-Assisted and Ln (OTf)_3-Catalyzed Homo-conjugate Addition of N-Heteroaromatics to Activated Cyclopropane Derivatives. (2008)
  • Author(s): Uddin, M-I., Mimoto, A., Nakano, K., Ichikawa, Y., Kotsuki, H
  • Journal Title: Tetrahedron Lett. 49 Pages: 5867-5870
  • Peer Reviewed
• [Journal Article] Synthesis of Conagenin and a-Methylserine.A Review (2008)
  • Author(s): Nakano, K.; Kotsuki, H.; Ichikawa, Y(第一著者)
  • Journal Title: Org.Prep.Proced.Int 40 Pages: 67-91
  • Peer Reviewed
• [Journal Article] Synthesis of (-)-Agelastatin A by [3.3]Sigmatropic Rearrangement of Allyl Cyanate (2007)
  • Author(s): Ichikawa, Y. ; Yamaoka, T. ; Nakano, K. ; Kotsuki, H.
  • Journal Title: Org. Lett 9 Pages: 2989-2992
  • Peer Reviewed
• [Journal Article] Synthesis of(-)-Agelastatin A by [3.3] Sigmatropic Rearrangement of Allyl Cyanate (2007)
  • Author(s): Ichikawa, Y.(第一著者); Yamaoka, T.; Nakano, K.; Kotsuki, H.
  • Journal Title: Org.Lett 9 Pages: 2989-2992
  • Peer Reviewed
• [Journal Article] Ichikawa, Y.Evolution, Development and Personal Experience of [3.3]Sigmatropic Rearrangement of Allyl Cyanate (2007)
  • Author(s): Ichikawa, Y.(第一著者)
  • Journal Title: Synlett Pages: 2927-2936
  • Peer Reviewed
• [Journal Article] A Novel Design of Roof-shaped Anthracene-fused Chiral Prolines as Organocatalysts for Asymmetric Mannich Reactions (2006)
  • Author(s): Sasaoka, A. ; Uddin, M-I. ; Shimomoto, A. ; Ichikawa, Y. ; Shiro, M. ; Kotsuki, H.
  • Journal Title: Tetrahedron : Asymmetry 17 Pages: 2963-2969
  • Peer Reviewed
• [Journal Article] A Stereocontrolled Route to Vicinal Diamines by Allyl Cyanate-to-isocyanate Rearrangement : Asymmetric Synthesis of anti (2R,3R)- and syn (2R,3S)-2,3-Diamino-butanoic Acids (2006)
  • Author(s): Ichikawa, Y. ; Egawa, H. ; Ito, T. ; Isobe, M. ; Nakano, K. ; Kotsuki, H.
  • Journal Title: Org. Lett. 8 Pages: 5737-5740
  • Peer Reviewed
• [Journal Article] Synthesis of Urea-tethered Disaccharides in Water (2006)
  • Author(s): Ichikawa, Y. ; Matsukawa, Y. ; Tamura, M. ; Ohara, F. ; Isobe, M. ; Kotsuki. H.
  • Journal Title: Asian J. Chem. 1 Pages: 717-723
  • Peer Reviewed
• [Journal Article] A New Approach to the Neoglycopeptides : Synthesis of Urea- and Carbamate-tethered N-Acetyl-D-glucosamine Amino Acid Conjugates (2006)
  • Author(s): Ichikawa, Y. ; Ohara, D., Kotsuki, H. ; Nakano, K.
  • Journal Title: Org. Lett. 8 Pages: 5009-5012
  • Peer Reviewed
• [Journal Article] High Pressure-Promoted Uncatalyzed Cyanation of Acetals Using Trimethylsilyl Cyanide as a Cyanide Source in Nitromethane (2006)
  • Author(s): K. Kumamoto, K. Nakano, Y. Ichikawa, and H. Kotsuki
  • Journal Title: Synlett Pages: 1968-1970
  • Peer Reviewed
• [Journal Article] Synthesis of Urea-tethered Neoglycoconjugates and Pseudo-oligosaccharides in Water (2006)
  • Author(s): Ichikawa, Y. ; Matsukawa, Y. ; Isobe, M.
  • Journal Title: J. Am. Chem. Soc. 128 Pages: 3934-3398
  • Peer Reviewed
• [Journal Article] Synthesis of(-)-(5R,6S)-6-Acetoxy-hexadecanolide Based on L-Proline-Catalyzed Asymmetric Aldol Reactions (2006)
  • Author(s): Ikishima, H. ; Sekiguchi, Y. ; Ichikawa, Y. ; H. Kotsuki, H.
  • Journal Title: Tetrahedron 62 Pages: 311-316
  • Peer Reviewed
• [Journal Article] Synthesis of Urea-tethered Neoglycoconjugates and Pseudo-oligosaccharides in Water. (2006)
  • Author(s): Ichikawa, Y., Matsukawa, Y., Isobe, M
  • Journal Title: J.Am.Chem.Soc. 128 Pages: 3934-3398
• [Journal Article] High Pressure-Promoted uncatalyzed Cyanation of Acetals Using Trimethylsilyl Cyanide as a Cyanide Source in Nitromethane (2006)
  • Author(s): K.Kumamoto, K.Nakano, Y.Ichikawa, H.Kotsuki.
  • Journal Title: Synlett 2006 Pages: 1968-1970
• [Journal Article] A New Approach to the Neoglycopeptidss : Synthesis of Urea-and Carbamate-tethered N-Acetyl-D-glucosamine Amino Acid Conjugates. (2006)
  • Author(s): Ichikawa, Y., Ohara, D., Kotsuki, H., Nakano, K.
  • Journal Title: Org.Lett. 8 Pages: 5009-5012
• [Journal Article] Synthesis of Urea-tethered Disaccharides in Water (2006)
  • Author(s): Ichikawa., Matsukawa, Y., Tamura, M., Ohara, F., Isobe, M., Kotsuki.H
  • Journal Title: Asian J.Chem. 1 Pages: 717-723
• [Journal Article] A Stereocontrolled Route to Vicinal Diamines by Allyl Cyanate-to-isocyanate Rearrangement : Asymmetric Synthesis of anti (2R,3R)-and syn (2R,3S)-2,3-Diaminobutanoic Acids (2006)
  • Author(s): Ichikawa, Y., Egawa, H., Ito, T., Isobe, M., Nakano, K., Kotsuki, H
  • Journal Title: Org.Lett. 8 Pages: 5737-5740
• [Journal Article] A Novel Design of Roof-shaped Anthracene-fused Chiral Prolines as Organocatalysts for Asymmetric Mannich Reactions (2006)
  • Author(s): Sasaoka, A., Uddin, M-I., Shimomoto, A., Ichikawa, Y., Shiro, M., Kotsuki, H
  • Journal Title: Tetrahedron : Asymmetry 17 Pages: 2963-2969
• [Journal Article] Stereoselective Allyl Amine Synthesis via Enantioselective Addition of Diethylzinc and [1,3]-Chirality Transfer ; Synthesis of Lentiginosine and Polyoxamic Acid Derivative (2005)
  • Author(s): Ichikawa, Y. ; Ito, T. ; Isobe, M.
  • Journal Title: Chem.-Eur. J. Pages: 1949-1957
  • Peer Reviewed
• [Journal Article] Allyl Cyanate-to-isocyanate Rearrangement for the Synthesis of Quaternary Stereocenter with Nitrogen Substituent (2005)
  • Author(s): Ichikawa, Y. ; Yamauchi, E. ; Isobe, M.
  • Journal Title: Biosci. Biotech. Biochem 69(5) Pages: 939-943
  • NAID: 130000030324
  • Peer Reviewed
• [Journal Article] Synthesis of(+)-Conagenin (2005)
  • Author(s): Matsukawa, Y. ; Isobe. M. ; Kotsuki. H. ; Ichikawa, Y.
  • Journal Title: J. Org. Chem 70 Pages: 5339-5341
  • Peer Reviewed
• [Journal Article] Total Synthesis of Glycocinnamoyl-Glycocinnamoylsperimicin D. (2005)
  • Author(s): Nishiyama, T. ; Ichikawa, Y. ;Isobe, M.
  • Journal Title: Angew. Chem. Int. Ed. Engl. 44 Pages: 4372-4375
  • Peer Reviewed
• [Journal Article] High-Pressure-Promoted Uncatalyzed Ketalization of Ketones and Oxy-Michael/Ketalization of Conjugated Enones (2005)
  • Author(s): Kumamoto, K. ; Ichikawa, Y. ; Kotsuki, H.
  • Journal Title: Synlett Pages: 2254-2256
  • Peer Reviewed
• [Journal Article] Stereoselective Allyl Amine Synthesis via Enantioselective Addition of Diethylzinc and [1,3]-Chirality Transfer ; Synthesis of Lentiginosine and Polyoxamic Acid Derivative. (2005)
  • Author(s): Ichikawa, Y., Ito, T., Isobe, M
  • Journal Title: Eur.J.Chem Pages: 1949-1957
• [Journal Article] Allyl Cyanate-to-isocyanate Rearrangement for the Synthesis of Quaternary Stereocenter with Nitrogen Substituent (2005)
  • Author(s): Ichikawa, Y., Yamauchi, E., Isobe, M.
  • Journal Title: Biosci.Biotech.Biochem 69 Pages: 939-943
  • NAID: 130000030324
• [Journal Article] Synthesis of (+)-Conagenin (2005)
  • Author(s): Matsukawa, Y., Isobe, M., Kotsuki, H., Ichikawa, Y
  • Journal Title: J.Org.Chem 70 Pages: 5339-5341
• [Journal Article] Total Synthesis of Glycocinnamoylsperimicin D (2005)
  • Author(s): Nishiyama, T., Ichikawa, Y., Isobe, M.
  • Journal Title: Angew.Chem.Int.Ed.Engl 44 Pages: 4372-4375
• [Journal Article] High-Pressure-Promoted Uncatalyzed Ketalization of Ketones and Oxy-Michael/Ketalization of Conjugated Enones (2005)
  • Author(s): Kumamoto, K., Ichikawa, Y., Kotsuki, H
  • Journal Title: Synlett Pages: 2254-2256
• [Presentation] 無保護糖を用いたウレアグリコントの合成研究 (2009)
  • Author(s): 草葉昌平, 市川善康
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 千葉船橋, 東京
• [Presentation] マンノスタチンAの合成研究 (2009)
  • Author(s): 崎山直人, 市川 善康
  • Organizer: 日本化学会 第89春季年会
  • Place of Presentation: 千葉船橋, 東京
• [Presentation] マンザシジン類の合成研究 (2009)
  • Author(s): 奥村 健, 市川 善康
  • Organizer: 日本化学会 第89春季年会
  • Place of Presentation: 千葉船橋, 東京
• [Presentation] イリジウム触媒を用いた新規1, 2-アミノアルコール合成法の開発 (2009)
  • Author(s): 山本 俊一, 市川 善康
  • Organizer: 日本化学会 第89春季年会
  • Place of Presentation: 千葉船橋, 東京
• [Presentation] イソニトリルのアノマー効果に関する研究 (2009)
  • Author(s): 渡邊瞳, 中野啓二, 市川善康
  • Organizer: 日本化学会 第89春季年会
  • Place of Presentation: 千葉船橋, 東京
• [Presentation] 2G2-51,アミノ糖系抗生物質グリコシンナスペリミシンDの合成研究 (2008)
  • Author(s): 楠本善史・原加那子・市川善康
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 立教大学池袋キャンパス,東京
• [Presentation] 4G3-10, 海洋天然物Pachastrissamineの合成研究 (2008)
  • Author(s): 松永健志・市川善康
  • Organizer: 第88春季年会
  • Place of Presentation: 立教大学池袋キャンパス,東京
• [Presentation] 転位反応を用いたマンザシジンの合成 (2008)
  • Author(s): 山本俊一・市川善康
  • Organizer: 第88春季年会
  • Place of Presentation: 立教大学池袋キャンパス,東京
• [Presentation] 4H3-43金属触媒を用いた新規1, 2-アミノアルコール合成法の開発 (2008)
  • Author(s): 山本俊一・市川善康
  • Organizer: 第88春季年会
  • Place of Presentation: 立教大学池袋キャンパス,東京
• [Presentation] 医薬品・農薬をつくるには (2007)
  • Author(s): 市川善康
  • Organizer: 第61期高知市民の大学
  • Year and Date: 2007-04-24
• [Presentation] 4H3-03 : 海洋天然物Pachastrissamine(Jaspine B)の合成研究 (2007)
  • Author(s): 松永健志・市川善康
  • Organizer: 日本化学会第87春季年会
  • Place of Presentation: 関西大学千里山キャンパス,大阪
• [Presentation] 4H3-04 : グリコシルイソシアナートを用いた糖-アミノ酸複合体の合成研究日本化学会 (2007)
  • Author(s): 渡邊瞳・小原史代・富田ゆみ子・市川善康
  • Organizer: 第87春季年会
  • Place of Presentation: 関西大学千里山キャンパス,大阪
• [Presentation] 2H4-09 :アミノ糖系抗生物質の合成研究 (2007)
  • Author(s): 楠本善史・原加那子・市川善康
  • Organizer: 日本化学会第87春季年会
  • Place of Presentation: 関西大学千里山キャンパス,大阪
• [Presentation] 2H4-10 : 海洋天然物アゲラスタチンAの全合成研究 (2007)
  • Author(s): 山岡具倫・市川善康
  • Organizer: 日本化学会第87春季年会
  • Place of Presentation: 関西大学千里山キャンパス,大阪
• [Presentation] 海洋天然物Pachastrissamineの合成研究 (2007)
  • Author(s): 松永健志・市川善康
  • Organizer: 第24回有機合成セミナー
  • Place of Presentation: 兵庫県淡路島
• [Presentation] P-56 : アミノ糖系抗生物質の合成研究 (2007)
  • Author(s): 楠本善史・奥村健・原加奈子・市川善康, 西山泰平・磯部稔
  • Organizer: 第49回天然有機化合物討論会
  • Place of Presentation: 札幌
• [Presentation] P-14海洋天然物Pachastrissamineの合成研究 (2007)
  • Author(s): 松永健志・市川善康
  • Organizer: 第24回有機合成化学セミナー
  • Place of Presentation: 淡路夢舞台国際会議場
• [Presentation] P-94 : Synthesis of Marine Alkakoid(-)-Agelastatin A Using Enantioselective (2007)
  • Author(s): Yoshiyasu Ichikawa, Tomonori Yamaoka
  • Organizer: Addition of Diethylzinc and Ring Closing Metathesis (OMCOS 14)
  • Place of Presentation: Nara
• [Presentation] 海洋天然物Pachastrissamine(Jaspine B)の合成研究 (2007)
  • Author(s): 松永 健志・市川 善康(代表者)
  • Organizer: 日本化学会 第87春季年会
  • Place of Presentation: 関西大学千里山キャンパス
• [Presentation] グリコシルイソシアナートを用いた糖-アミノ酸複合体の合成研究 (2007)
  • Author(s): 渡邊 瞳・小原 史代・富田 ゆみ子・市川 善康(代表者)
  • Organizer: 日本化学会 第87春季年会
  • Place of Presentation: 関西大学千里山キャンパス
• [Presentation] アミノ糖系抗生物質の合成研究 (2007)
  • Author(s): 楠本 善史・原加 那子・市川 善康(代表者)
  • Organizer: 日本化学会 第87春季年会
  • Place of Presentation: 関西大学千里山キャンパス
• [Presentation] 海洋天然物アゲラスタチンAの全合成研究 (2007)
  • Author(s): 山岡 具倫・市川 善康(代表者)
  • Organizer: 日本化学会 第87春季年会
  • Place of Presentation: 関西大学千里山キャンパス
• [Presentation] アミノ糖系抗生物質の合成研究 (2007)
  • Author(s): 楠本 善史・奥村 健・原加 奈子・市川 善康(代表者)・西山 泰平・磯部 稔
  • Organizer: 第49回天然有機化合物討論会
  • Place of Presentation: 札幌
• [Presentation] Synthesis of Marine Alkakoid(-)-Agelastatin A Using Enantioselective Addition of Diethylzinc and Ring Closing Metathesis (2007)
  • Author(s): Yoshiyasu Ichikawa (代表者), Tomonori Yamaoka
  • Organizer: OMCOS 14
  • Place of Presentation: Nara
• [Presentation] 3L3-49 : [3.3]-シグマトロピー転位反応を用いた2, 3-ジアミノブタン酸の合成研究 (2006)
  • Author(s): 江川晴香, 市川善康
  • Organizer: 日本化学会第886春季年会
  • Place of Presentation: 千葉船橋
• [Presentation] 3L3-5 : 海洋天然物アゲラスタチンAの合成研究 (2006)
  • Author(s): 山岡具倫, 市川善康
  • Organizer: 日本化学会第86春季年会
  • Place of Presentation: 千葉船橋
• [Presentation] 4L2-1 : 人口糖ペプチドの合成研究 (2006)
  • Author(s): 小原史代, 市川善康
  • Organizer: 日本化学会第86春季年会
  • Place of Presentation: 千葉船橋
• [Presentation] 4L2-16 : アミノ糖系抗生物質の合成研究 (2006)
  • Author(s): 楠本善史, 原加那子, 市川善康
  • Organizer: 日本化学会第86春季年会
  • Place of Presentation: 千葉船橋
• [Presentation] P-5 : Ally1 Cyanate-to-isocyanate Rearrangement in Natural Product Synthesis (2006)
  • Author(s): Y. Ichikawa, H. Egawa, Y. Matsukawa, T. Ito, and M. Isobe
  • Organizer: International Conference on Biodiversity and Natural Products (ICOB-5 & ISCNP-25)
  • Place of Presentation: Kyoto
• [Presentation] P-413 : Synthetic Studies of Agelastatin A (2006)
  • Author(s): T. Yamaoka and Y. Ichikawa
  • Organizer: International Conference on Biodiversity and Natural Products (ICOB-5 & ISCNP-25)
  • Place of Presentation: Kyoto
• [Presentation] P-425 Synthetic Study of the Nucleoside Antibiotic Polyoxin J (2006)
  • Author(s): S. Miyauchi, Y. Ichikawa, and K. Nakano
  • Organizer: International Conference on Biodiversity and Natural Products (ICOB-5 & ISCNP-25)
  • Place of Presentation: Kyoto
• [Presentation] P-38 : ウレアグリコシド結合をもつ人工ペプチド・オリゴ糖の合成研究 (2006)
  • Author(s): 小原史代・田村真理・市川善康, 松川洋平・磯部稔
  • Organizer: 第48回天然有機化合物討論会
  • Place of Presentation: 仙台