Total syntheses and reaction developments on the basis of axial-rich sugars

2012 Fiscal Year Final Research Report

• Project/Area Number: 22550047
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Kwansei Gakuin University
• Principal Investigator: YAMADA Hidetoshi 関西学院大学, 理工学部, 教授 (90200732)
• Project Period (FY): 2010 – 2012
• Keywords: 合成有機化学 / 天然物合成

Research Abstract

Utilizing the unique property of sugar derivatives, which conformation were locked into the axial-rich conformation, we developed (1) synthesis of ellagitannins and (2) stereoselective glycosylation reactions. In the research for (1), new synthetic routes for the axial-rich ellagitannins were developed to increase the lead in the aria of ellagitannin synthesis. For (2), highly α-selective glycosylations were developed by applying the sugars locked to the axial-rich conformations.

Research Products

• [Journal Article] Roxbin B is Cuspinin; Structural Revision and Total Synthesis (2013)
  • Author(s): Yamaguchi, S.; Hirokane, T.; Yoshida, T.; Tanaka, T.; Hatano, T.; Ito, H.; Nonaka, G.; Ya mada, H.
  • Journal Title: J. Org. Chem. Volume: 78
  • DOI: doi:10.1021/jo400562k
  • Peer Reviewed
• [Journal Article] High Yield Total Synthesis of (-)-Strictinin through Intramolecular Coupling of Gallates (2013)
  • Author(s): Michihata, N.; Kaneko, Y.; Kasai, Y.; Tanigawa, K.;Hirokane, T.; Higasa, S.; Ya mada, H.
  • Journal Title: J. Org. Chem Volume: 78 Pages: 4319-4328
  • DOI: doi:10.1021/jo4003135
  • Peer Reviewed
• [Journal Article] Total Synthesis of the Proposed Structure of Roxbin B; the Nonidentical Outcome (2012)
  • Author(s): Yamaguchi, S.; Ashikaga, Y.; Nishii, K.; Ya mada, H.
  • Journal Title: Org. Lett. Volume: 14 Pages: 5928-5931
  • DOI: doi:10.1021/ol302845n
  • Peer Reviewed
• [Journal Article] Total Synthesis of (+)-Davidiin, Kasai (2012)
  • Author(s): Y.; Michihata, N.; Nishimura. H.; Hirokane, T.; Ya mada, H.
  • Journal Title: Angew. Chem. Int. Ed. Volume: 51 Pages: 8026-8029.
  • DOI: doi:10.1002/anie.201203305. Highlighted in Synfacts 2012,8, 1062.,doi:10.1055/s-0032-1317276.
  • Peer Reviewed
• [Journal Article] Completely β-Selective Glycosylation Using3,6-O-(O-Xylylene)-Bridged Axial-Rich Glucosyl Fluoride. (2012)
  • Author(s): Okada, Y.; Asakura, N.; Bando, M.; Ashikaga, Y.; Ya mada, H.
  • Journal Title: J. Am. Chem. Soc. Volume: 134 Pages: 6940-6943.
  • DOI: doi:10.1021/ja301480g.
  • Peer Reviewed
• [Journal Article] Strategies and Methods for the Total Synthesis of Ellagitannins. (2012)
  • Author(s): Ya mada, H.; Hirokane, T.; Asakura, N.; Kasai, Y.; Nagao, K.
  • Journal Title: Curr. Org. Chem. Volume: 16 Pages: 578-604
  • DOI: doi:10.2174/138527212799859426.
  • Peer Reviewed
• [Journal Article] Synthesis of Chiral and Modifiable Hexahydroxydiphenoyl Compounds. (2011)
  • Author(s): Asakura, N.; Fujimoto, S.; Michihata, N.; Nishii, K.; Imagawa, H.; Ya mada, H.
  • Journal Title: J. Org. Chem. Volume: 76 Pages: 9711-9719
  • DOI: doi:10.1021/jo201750d.
  • Peer Reviewed
• [Journal Article] O-Glycosylation Reaction Using Axial-Rich Glycosyl Donors. (2011)
  • Author(s): Ya mada, H.
  • Journal Title: Trends Glycosci. Glycotechnol. Volume: 123 Pages: 122-133
  • DOI: doi:410.4052/tigg.23.122.
  • Peer Reviewed
• [Journal Article] Molecular Sieves 5A as an Acidic Reagent: the Discovery and Applications. (2011)
  • Author(s): Asakura, N.; Hirokane, T.; Hoshida, H.; Ya mada, H.
  • Journal Title: Tetrahedron Lett. Volume: 52 Pages: 534-537
  • DOI: doi:10.1016/j.tetlet.2010.11.113.
  • Peer Reviewed
• [Presentation] 3,6-O-[ビベンジル-2,2'-ビス(メチレン)]架橋糖を用いた高α選択的グルコシル化反応 (2013)
  • Author(s): 平田恭章・足利是貴・山田英俊
  • Organizer: 第93回日本化学会年会
  • Place of Presentation: 立命館大学びわこくさつキャンパス
  • Year and Date: 2013-03-23
• [Presentation] ss-ペンタガロイルグルコース誘導体のアリールカップリングによる3,6-HHDP架橋体の単離 (2013)
  • Author(s): 久米裕二・芦辺成矢・上野友理・岩下孝・山田英俊
  • Organizer: 第93回日本化学会年会
  • Place of Presentation: 立命館大学びわこくさつキャンパス
  • Year and Date: 2013-03-23
• [Presentation] 3,6-O-(o-キシリレン)架橋によりアキシアル・リッチな立体配座としたフッ化糖を用いるβ-グリコシル化反応 (2012)
  • Author(s): 山田英俊
  • Organizer: 第10回糖鎖科学コンソーシアムシンポジウム
  • Place of Presentation: 東京コンファレンスセンター(品川)
  • Year and Date: 2012-11-30
• [Presentation] Total Synthesis of anAxial-Rich Ellagitannin, Corilagin (2012)
  • Author(s): Yamada, H.
  • Organizer: 13thInternational Symposium on NaturalProduct Chemistry
  • Place of Presentation: University of Karachi, Pakistan,oral,Invited speaker
  • Year and Date: 2012-09-23
• [Presentation] ラゲルスタンニンCの全合成とロキシビン Bの構造訂正・全合成 (2012)
  • Author(s): 山口左有里、金子由季、広兼司、足利是貴、西井健太郎、道畑直起、山田英俊
  • Organizer: 第54回天然有機化合物討論会
  • Place of Presentation: 東京農業大学世田谷キャンパス
  • Year and Date: 2012-09-20
• [Presentation] Totalsynthesis of praecoxin B (2012)
  • Author(s): Hirokane, T.; Naoki, M.; Asakura, N.; Mitamura, T.; Yamada, H
  • Organizer: 26thInternational Conference on Polyphenols
  • Place of Presentation: Firenche, Italy,poster,Awarded a poster prize
  • Year and Date: 2012-07-23
• [Presentation] Synthesis of Chiral and Modifiable Hexahydroxydiphenoyl Compounds (2012)
  • Author(s): Asakura, N.; Fujimoto, S.; Michihata, N.; Nishii, K.; Imagawa, H.; Yamada, H
  • Place of Presentation: Firenche, Italy
  • Year and Date: 2012-07-23
• [Presentation] 軸不斉HexaHydroxyDiPhenoyl基の使いかた (2012)
  • Author(s): 山田英俊
  • Organizer: 第2回有機分子構築法夏の勉強会
  • Place of Presentation: ラフォーレ蔵王リゾート&スパ
  • Year and Date: 2012-05-19
• [Presentation] 2,4-O(-2,2'-ビベンジルビス(メチレン)架橋を用いた (2012)
  • Author(s): 足利是貴・廣兼司・山田英俊
  • Organizer: D-グルコースの環立体配座制御
  • Place of Presentation: 慶應義塾大学
  • Year and Date: 2012-03-28
• [Presentation] RoxbinBの全合成研究 (2012)
  • Author(s): 山口左有里・足利是貴・山田英俊
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶應義塾大学
  • Year and Date: 2012-03-27
• [Presentation] ss-ペンタガロイルグルコース誘導体のヘキサヒドロキシジフェノイル架橋 (2011)
  • Author(s): 芦辺成矢,藤本翔平,上野友理,広兼司,久米裕二,山田英俊
  • Organizer: 第53回天然有機化合物討論会
  • Place of Presentation: 大阪国際交流センター
  • Year and Date: 2011-09-30
• [Presentation] D-グルコン酸部分を持つエラジタンニン、ラゲルスタンニンCの合成研究 (2011)
  • Author(s): 金子由季・丹田健太郎・道畑直起・山田英俊
  • Organizer: 日本化学会第91春季年会
  • Year and Date: 2011-03-11
• [Presentation] 3,6-O-(o-キシリレン)架橋糖を用いた高立体選択的グルコシル化反応 (2011)
  • Author(s): 本山敦之・足利是貴・山田英俊
  • Organizer: 日本化学会第91春季年会
  • Year and Date: 2011-03-11
• [Presentation] Total synthesis of(-)-strictinin in high overall yield (2010)
  • Author(s): Naoki Michihata, Noriaki Asakura, Hidetoshi Yamada
  • Organizer: Pacifichem 2010
  • Place of Presentation: HonoluluHawaii
  • Year and Date: 2010-12-16
• [Presentation] アキシアル・リッチ糖を用いたβ-グルコシドの製造 (2010)
  • Author(s): 山田英俊
  • Organizer: 新技術説明会
  • Place of Presentation: JSTホール(東京)
  • Year and Date: 2010-11-19
• [Presentation] (+)-PraecoxinB,(-)-Strictininの全合成 (2010)
  • Author(s): 廣兼司,道畑直起,朝倉典昭,葛西祐介,谷川康太郎,三田村隆史,山田英俊
  • Organizer: 第52回天然有機化合物討論会
  • Place of Presentation: グランシップ静岡
  • Year and Date: 2010-09-29
• [Presentation] Synthesis of 1,2,4-Orthoacetyl-_-D-Glucopyranose Utilizing Molecular Sieves (2010)
  • Author(s): N. Asakura, H. Hoshida, H. Yamada
  • Organizer: The 25th lnternational Carbohydrate Symposium
  • Place of Presentation: 幕張メッセ
  • Year and Date: 2010-08-03
• [Presentation] 6-ヘキサヒドロキシジフェノイル架橋エラジタンニン、(+)-Davidiinの5段階合成 (2010)
  • Author(s): 芦辺成矢・朝倉典昭・藤本翔平・山田英俊,1
  • Organizer: 第37回有機反応懇談会
  • Place of Presentation: 京都大学宇治キャンパス
  • Year and Date: 2010-08-02
• [Presentation] (-)-コリラジン全合成の単段階化とモレキュラーシーブ5Aの酸性反応剤としての利用 (2010)
  • Author(s): 山田英俊
  • Organizer: 第一回有機分子構築法夏の勉強会
  • Place of Presentation: ラフォーレ蔵王リゾート&スパ
  • Year and Date: 2010-05-23
• [Patent(Industrial Property Rights)] 3,6-O-架橋反転ピラノース化合物及び α-O-ピラノシドの製造方法 (2013)
  • Inventor(s): 山田英俊
  • Industrial Property Rights Holder: 学校法人関西学院
  • Industrial Property Number: 特許,特願 2013-028518
  • Filing Date: 2013-02-18
• [Patent(Industrial Property Rights)] 3,6-O-架橋反転ピラノース化合物及びss-O-ピラノシドの製造方法 (2013)
  • Inventor(s): 山田英俊、朝倉典昭、岡田康則
  • Industrial Property Rights Holder: 学校法人関西学院
  • Industrial Property Number: 登録,特許第5258798号
  • Acquisition Date: 2013-05-02
• [Patent(Industrial Property Rights)] 2,4-O-架橋反転ピラノース化合物 (2012)
  • Inventor(s): 山田英俊
  • Industrial Property Rights Holder: 学校法人関西学院
  • Industrial Property Number: 特許,特願 2012-032663
  • Filing Date: 2012-02-17