Development and Application of Highly Stereoselective Aldol Reactions Using Chiral Amide

2012 Fiscal Year Final Research Report

• Project/Area Number: 22390004
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Tokyo University of Science
• Principal Investigator: KOBAYASHI Susumu 東京理科大学, 薬学部, 教授 (70101102)
• Co-Investigator(Renkei-kenkyūsha): SUZUKI Takahiro 東京理科大学, 薬学部, 助教 (80367052)
• Project Period (FY): 2010 – 2012
• Keywords: 合成化学 / 天然物合成

Research Abstract

Diastereoselective reactions using chiral amide have extensively been utilized in the chiral synthesis of complex molecules in these decades.In this context, we have developed two types of diastereoselective aldol reactions. In the present investigation, we focused on (1) further improvement of vinylogous Mukaiyama aldol reaction, (2) general applicability of the stereocontrol of 1,2-diol including tertiary alcohol, and (3) application to biologically significant naturally occurring compounds.

Research Products

• [Journal Article] Unexpected Diels-Alder/Carbonylene Cascade toward the Biomimetic Synthesis of Chloropupukeananin (2013)
  • Author(s): T. Suzuki, Y. Miyajima, K. Suzuki, K. Iwakiri, M. Koshimizu, G. Hirai, M. Sodeoka, S.Kobayashi
  • Journal Title: Organic Letters Volume: 15 Pages: 1748-1751
  • DOI: DOI:10.1021/ol400549q
  • Peer Reviewed
• [Journal Article] Synthetic Study of Pyrrocidines: First Entry to the Decahydrofluorene Core of Pyrrocidines (2012)
  • Author(s): R. Tanaka, K. Ohishi, N. Takanashi, T.Nagano, H. Suizu, T. Suzuki, S. Kobayashi
  • Journal Title: Organic Letters Volume: 14 Pages: 4886-4889
  • DOI: DOI:10.1021/ol3022116
  • Peer Reviewed
• [Journal Article] Concise Total Synthesis of (-)-Myxalamide A (2012)
  • Author(s): K. Fujita, R. Matsui, T. Suzuki, S. Kobayashi
  • Journal Title: Angewandte Chemie Int. Ed. Volume: 51 Pages: 7271-7274
  • DOI: DOI:10.1002/anie.201203093
  • Peer Reviewed
• [Journal Article] Determination of the Absolute Structure of (+)-Akaterpin (2012)
  • Author(s): H. Hosoi, N. Kawai, H. Hagiwara, T. Suzuki, A. Nakazaki, K. Takao, K. Umezawa, S.Kobayashi
  • Journal Title: Chem. Pharm. Bull Volume: 60 Pages: 137-143
  • DOI: DOI:10.1248/cpb.60.137
  • Peer Reviewed
• [Journal Article] A Synthetic Study of Atropurpuran: Construction of a Pentacyclic Framework by an Intramolecular Reverse-Electron-Demand Diels-Alder Reaction (2011)
  • Author(s): T. Suzuki, A. Sasaki, N. Egashira, S.Kobayashi
  • Journal Title: Angewandte Chemie Int. Ed. Volume: 50 Pages: 9177-9179
  • DOI: DOI:10.1002/anie.201103950
  • Peer Reviewed
• [Journal Article] Synthesis and determination of the relative structure of akaterpin, a potent inhibitor of PI-PLC (2011)
  • Author(s): H. Hosoi, N. Kawai, H. Hagiwara, T. Suzuki, A. Nakazaki, K. Takao, K. Umezawa, S.Kobayashi
  • Journal Title: Tetrahedron Letters Volume: 52 Pages: 4961-4964
  • DOI: DOI:10.1016/j.tetlet.2011.07.079
  • Peer Reviewed
• [Journal Article] Different Modes of Cyclization in Zoanthamine Alkaloid System, Bisaminal versus Spiroketal Formation (2011)
  • Author(s): T. Nakajima, D. Yamashita, K. Suzuki, A.Nakazaki, T. Suzuki, S. Kobayashi
  • Journal Title: Organic Letters Volume: 13 Pages: 2980-2983
  • DOI: DOI:10.1021/ol200486c
  • Peer Reviewed
• [Journal Article] Stereoselective Vinylogous Mukaiyama Aldol Reaction of α-Haloenals (2011)
  • Author(s): Y. Iwasaki, R. Matsui, T. Suzuki, A. Nakazaki, S. Kobayashi;
  • Journal Title: Chem. Pharm. Bull. Volume: 59 Pages: 522-524
  • DOI: DOI:10.1248/cpb.59.522
  • Peer Reviewed
• [Journal Article] The second generation synthesis of (+)-pseudodeflectusin (2011)
  • Author(s): Y. Sato, K. Kuramochi, T. Suzuki, A.Nakazaki, S. Kobayashi
  • Journal Title: Tetrahedron Letters Volume: 52 Pages: 626-629
  • DOI: DOI:10.1016/j.tetlet.2010.11.153
  • Peer Reviewed
• [Journal Article] Convergent Total Synthesis of (+)-TMC-151C Using Vinylogous Mukaiyama Aldol Reaction and Ring-Closing Metathesis (2011)
  • Author(s): R. Matsui, K. Seto, Y. Sato, T. Suzuki, A.Nakazaki, S. Kobayashi
  • Journal Title: Angewandte Chemie Int. Ed. Volume: 50 Pages: 680-683
  • DOI: DOI:10.1002/anie.201006230
  • Peer Reviewed
• [Journal Article] Total Synthesis of (+)-Nafuredin-γ Using a Highly Stereoselective Ti-mediated Aldol Reaction (2011)
  • Author(s): Y. Onodera, T. Suzuki, S. Kobayashi
  • Journal Title: Organic Letters Volume: 13 Pages: 50-53
  • DOI: DOI:10.1021/ol102501k
  • Peer Reviewed
• [Journal Article] Unusual Selective E-Olefin Forming 8-Membered Ring Closing Metathesis (2010)
  • Author(s): R. Matsui, K. Seto, K. Fujita, T. Suzuki, A.Nakazaki, S. Kobayashi
  • Journal Title: Angewandte Chemie Int. Ed. Volume: 49 Pages: 10068-10073
  • DOI: DOI:10.1002/anie.201004746
  • Peer Reviewed
• [Journal Article] Concise Approach to Pupukeanane Skeleton: Synthetic Study of Chloropupukeananin (2010)
  • Author(s): T. Suzuki, S. Kobayashi
  • Journal Title: Organic Letters Volume: 12 Pages: 2920-2923
  • DOI: DOI:10.1021/ol100935w
  • Peer Reviewed
• [Journal Article] Second-Generation Total Synthesis of (-)-Diversifolin (2010)
  • Author(s): K. Tsuboi, T. Nakamura, T. Suzuki, A.Nakazaki, S. Kobayashi
  • Journal Title: Tetrahedron Letters Volume: 51 Pages: 1876-1879
  • DOI: DOI:10.1016/j.tetlet.2010.02.012
  • Peer Reviewed
• [Presentation] 逆電子要請型Diels-Alder反応による多環性骨格の構築 (2012)
  • Author(s): 小林 進
  • Organizer: 平成24年度後期有機合成化学講習会
  • Place of Presentation: 薬学会館、東京
  • Year and Date: 2012-12-11
• [Presentation] ビニロガス向山アルドール反応の開発と天然物合成への応用 (2012)
  • Author(s): 小林 進
  • Organizer: 東京農工大学有機化学セミナー
  • Place of Presentation: 東京農工大学工学部、東京
  • Year and Date: 2012-12-10
• [Presentation] Incensol Acetateの合成研究 (2012)
  • Author(s): 木村真菜、正木すなみ、朝比奈裕宗、鈴木孝洋、小林 進
  • Organizer: 第64回有機合成化学協会関東支部シンポジウム
  • Place of Presentation: 長岡科学技術大学、新潟
  • Year and Date: 2012-12-01
• [Presentation] ビニロガス向山アルドール反応を用いたMethynolideの効率的な合成研究 (2012)
  • Author(s): 藤村正貴、松井亮介、鈴木孝洋、小林 進
  • Organizer: 第64回有機合成化学協会関東支部シンポジウム
  • Place of Presentation: 長岡科学技術大学、新潟
  • Year and Date: 2012-12-01
• [Presentation] 古くても伝えたい二つのこと:20代と30代の時の研究から (2012)
  • Author(s): 小林 進
  • Organizer: 第64回有機合成化学協会関東支部シンポジウム
  • Place of Presentation: 長岡科学技術大学、新潟
  • Year and Date: 2012-12-01
• [Presentation] 新しい方法論の開発に基づく生物活性天然物の合成研究 (2012)
  • Author(s): 小林 進
  • Organizer: 第30回メディシナルケミストリーシンポジウム
  • Place of Presentation: タワーホール船堀、東京
  • Year and Date: 2012-11-29
• [Presentation] 天然物の全合成におけるモデル化合物設定の難しさ (2012)
  • Author(s): 小林 進
  • Organizer: 早稲田大学理工学術院講演会
  • Place of Presentation: 早稲田大学、東京
  • Year and Date: 2012-10-19
• [Presentation] Synthetic Organic Chemistry as a Fundamental and a Tool in Bioscience (2012)
  • Author(s): S. Kobayashi
  • Organizer: 2012 Bilateral Symposium of Tokyo University of Science and Sichuan University
  • Place of Presentation: 成都・四川大学、中国
  • Year and Date: 2012-08-11
• [Presentation] 新しい方法論の開発と天然物合成への応用 (2012)
  • Author(s): 小林 進
  • Organizer: 理研シンポジウム 第7回有機合成化学のフロンティア
  • Place of Presentation: 理化学研究所、埼玉
  • Year and Date: 2012-07-06
• [Presentation] Development of New Methodology and Application to Natural Product Synthesis (2012)
  • Author(s): S. Kobayashi
  • Organizer: ESPCI Organic Chemistry Seminar
  • Place of Presentation: Ecole Superieure de Physique de Chimie Industrielles (ESPCI), Paris, France
  • Year and Date: 2012-06-22
• [Presentation] Development of New Methodology and Application to Natural Product Synthesis (2012)
  • Author(s): S. Kobayashi
  • Organizer: Mini-Symposium at Leibniz University Hannover
  • Place of Presentation: Leibniz University Hannover, Hannover, German
  • Year and Date: 2012-06-19
• [Presentation] アトロプルプランの合成研究 (2012)
  • Author(s): 鈴木孝洋、佐々木綾、江頭直樹、小林 進
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶応義塾大学・横浜
  • Year and Date: 2012-03-26
• [Presentation] 天然物合成における骨格構築の醍醐味 (2012)
  • Author(s): 小林 進
  • Organizer: 名古屋大学工学研究科特別講演会
  • Place of Presentation: 名古屋大学
  • Year and Date: 2012-01-12
• [Presentation] Chloropupukeananinの合成研究 (2011)
  • Author(s): 鈴木孝洋、岩切佳那子、宮嶋ゆりあ、鈴木要、石見遼、小清水正樹、小林 進
  • Organizer: 第100回有機合成シンポジウム
  • Place of Presentation: 早稲田大学、東京
  • Year and Date: 2011-11-10
• [Presentation] Development of Stereoselective Vinylogous Mukaiyama Aldol Reaction and Application to Natural Product Synthesis (2011)
  • Author(s): S. Kobayashi
  • Organizer: 1st Scottish-Japanese Symposium in Organic Chemistry
  • Place of Presentation: Glasgow,Scotland
  • Year and Date: 2011-09-08
• [Book] (2012)
  • Author(s): 小林 進,三巻祥浩
  • Total Pages: 137
  • Publisher: 培風館
• [Remarks] 東京理科大学薬学部小林研究室
  • URL: http://www.rs.noda.tus.ac.jp/kobalab/index.html