Synthesis of macrolactin A and itsderivatives using Z-selective intramolecular Horner-Wadsworth-Emmons reaction

• Project/Area Number: 22550095
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Gifu University
• Principal Investigator: ANDO Kaori 岐阜大学, 工学部, 教授 (70211018)
• Co-Investigator(Renkei-kenkyūsha): OKA Natsuhisa 岐阜大学, 工学部, 准教授 (50401229)
• Project Period (FY): 2010 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2012: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2011: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2010: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
• Keywords: マクロラクチンA / 分子内HWE反応 / Z-選択的 / 誘導体合成 / 分子内ＨＷＥ反応 / Ｚ選択性 / マクロラクチンＡ / 合成化学 / Macrolactin A / Z選択的 / ホスホネート試薬 / 大環状ラクトン / Macrolactin A誘導体

Research Abstract

Intramolecular Horner-Wadsworth-Emmons reaction of the substrates (ArO)2P(O)CH2CO2…CHO gave the 12- to 18-membered-ring Z-lactones highly selectively. While, the substrates (RO)2P(O)CH2CO2…CHO gave the E-lactones highly selectively. The synthesis of a macrolactin A derivative was performed by this method.

Research Products

• [Journal Article] Highly Z-Selective Synthesis of α,β- Unsaturated Nitriles Using Horner- Wadsworth-Emmons Reaction. (2013)
  • Author(s): Ando, K.; Okumura, M.; Nagaya, S.
  • Journal Title: Tetrahedron Lett. Volume: 54 Pages: 2026-2028
  • Peer Reviewed
• [Journal Article] Z-Selective intramolecular Horner-Wadsworth-Emmons reaction for the synthesis of macrocyclic alkenes. (2011)
  • Author(s): Ando, K.; Sato, K.
  • Journal Title: Tetrahedron Lett. Volume: 52 Pages: 1284-1287
  • Peer Reviewed
• [Journal Article] Highly E-selective solvent-free Horner-Wadsworth-Emmons reaction catalyzed by DBU. (2011)
  • Author(s): Ando, K.; Yamada, K.
  • Journal Title: Green Chemistry Volume: 13 Pages: 1143-1146
  • Peer Reviewed
• [Journal Article] Highly E-selective solvent-free Horner-Wadsworth-Emmons reaction catalyzed by DBU (2011)
  • Author(s): Ando, K.; Yamada, K.
  • Journal Title: Green Chemistry Volume: 13 Pages: 1143-1146
  • Peer Reviewed
• [Journal Article] Z-Selective intramolecular Homer-Wadsworth-Emmons reaction for the synthesis of macrocyclic alkenes (2011)
  • Author(s): AndoK.; Sato, K.
  • Journal Title: Tetrahedron Letters Volume: 52 Issue: 12 Pages: 1284-1287
  • DOI: 10.1016/j.tetlet.2011.01.043
  • Peer Reviewed
• [Journal Article] Facile synthesis of α-amino phosphonates in water by Kabachnik-Fields reaction using maenesium dodecyl sulfate (2011)
  • Author(s): Ando, K.; Egami, T.
  • Journal Title: Heteroatom Chemistry Volume: 22 Pages: 358-362
  • Peer Reviewed
• [Journal Article] Structure and Dynamic Behavior of Neutral Hexacoordinate Antimony Compounds with Intramolecular Coorination (2011)
  • Author(s): Yamanichi, H.; Matsukawa, S.; Kojima, S.; Ando, K.; Yamamoto, Y.
  • Journal Title: Heteroatom Chemistry Volume: 22 Pages: 553-561
  • Peer Reviewed
• [Journal Article] DFT and ONIOM Study on the Alkylation of the Lithium Enolate in Solution : Microsolvation Cluster Models for CH_2=CHOLi+CH_3Cl+ (THF)_<0-6> (2011)
  • Author(s): Ando, K.; Morokuma, K.
  • Journal Title: Theoretical Chemistry Accounts Volume: 130 Issue: 2-3 Pages: 323-331
  • DOI: 10.1007/s00214-011-0981-1
  • Peer Reviewed
• [Journal Article] Highly Enantioselective Cyclopropenation Reaction of 1-Alkynes with α-Alkyl-α-diazoesters Catalyzed by Dirhodium(II) Carboxylates (2011)
  • Author(s): Goto,T.; Takeda,K.；Shimada,N.;Nambu,H.; Anada,M;Shiro.M; Ando,.K; Hashimoto,S.
  • Journal Title: Angew. Chem. Int. Ed. Volume: 50 Issue: 30 Pages: 6803-6808
  • DOI: 10.1002/anie.201101905
  • URL: http://dx.doi.org/
  • Peer Reviewed
• [Journal Article] Z-Selective intramolecular Horner-Wadsworth-Emmons reaction for the synthesis of macroc clic alkenes. (2011)
  • Author(s): Ando, K., Sato, K.
  • Journal Title: Tetrahedron Letters Volume: 52 Pages: 1284-1287
  • Peer Reviewed
• [Journal Article] Solvent-free Horner-Wadsworth-Emmons reaction using DBU. (2010)
  • Author(s): Ando, K.; Yamada, K.
  • Journal Title: Tetrahedron Lett. Volume: 51 Pages: 3297-3299
  • Peer Reviewed
• [Journal Article] New polymer- supported phosphonate reagents for the synthesis of Z-α,β-unsaturated esters. (2010)
  • Author(s): Ando, K.; Suzuki, Y.
  • Journal Title: Tetrahedron Lett. Volume: 51 Pages: 2323-2325
  • Peer Reviewed
• [Journal Article] Z-selective Intramolecular Horner- Wadsworth-Emmons Reaction for the Synthesis of Macrocyclic Lactones. (2010)
  • Author(s): Ando, K.; Narumiya, K.; Takada, H.; Teruya, T.
  • Journal Title: Org. Lett. Volume: 12 Pages: 1460-1463
  • Peer Reviewed
• [Journal Article] Z-selective Intramolecular Horner-Wadsworth-Emmons Reaction for the Synthesis of Macrocyclic Lactones. (2010)
  • Author(s): Ando, K., Narumiya, K., Takada, H., Teruya, T.
  • Journal Title: Organic Letters Volume: 12 Pages: 1460-1463
  • Peer Reviewed
• [Journal Article] New polymer-supported phosphonate reagents for the synthesis of Z-α, β-unsaturated esters. (2010)
  • Author(s): Ando, K., Suzuki, Y.
  • Journal Title: Tetrahedron Letters Volume: 51 Pages: 2323-2325
  • Peer Reviewed
• [Presentation] 「大環状ラクトン合成のための高Z選択的分子内HWE反応の開発」口頭発表 (2013)
  • Author(s): 江口勇馬、安藤香織
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 滋賀
  • Year and Date: 2013-03-23
• [Presentation] 新しいJulia-Kocienskiオレフィン化試薬の開発, 口頭発表 (2013)
  • Author(s): 河野大喜、瀬見井 優、安藤香織
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 滋賀
  • Year and Date: 2013-03-22
• [Presentation] 大環状ラクトン合成のための高Ｚ選択的分子内ＨＷＥ反応の開発 (2013)
  • Author(s): 江口勇馬、安藤香織
  • Organizer: 日本化学会第93回春季年会（2013）、滋賀
  • Place of Presentation: 立命館大学びわこ・くさつキャンパス
• [Presentation] 新しいJulia-Kocienskiオレフィン化試薬の開発, ポスター (2012)
  • Author(s): 河野大喜、瀬見井優、安藤香織
  • Organizer: 第43回中部地化学関係学協会支部連合秋季大会
  • Place of Presentation: 名古屋
  • Year and Date: 2012-11-10
• [Presentation] 大環状ラクトン合成のための高Z選択的分子内HWE反応の開発, ポスター (2012)
  • Author(s): 江口勇馬、安藤香織
  • Organizer: 第43回中部地化学関係学協会支部連合秋季大会
  • Place of Presentation: 名古屋
  • Year and Date: 2012-11-10
• [Presentation] オレフィンの立体化学を制御する (2012)
  • Author(s): 安藤香織
  • Organizer: 第12回有機合成化学談話会
  • Place of Presentation: 湯河原
  • Year and Date: 2012-09-21
• [Presentation] One-pot preparations of Z-α,β-unsaturated esters via either reduction or oxidation followed by Z-selective HWE reaction (2012)
  • Author(s): Kaori Ando, Chika Takaba, Mami Takao
  • Organizer: The 6th Takeda Science Foundation Symposium on Pharma Sciences
  • Place of Presentation: Osaka
  • Year and Date: 2012-09-13
• [Presentation] オレフィンの立体化学を制御する (2012)
  • Author(s): 安藤香織
  • Place of Presentation: 岡山理科大学理学部
  • Year and Date: 2012-09-03
• [Presentation] アルコールの酸化とHWE反応によるZ-α,β-不飽和エステルのワンポット合成, ポスター (2012)
  • Author(s): 鷹羽千花、安藤香織
  • Organizer: 日本プロセス化学会2012サマーシンポジウム
  • Place of Presentation: 京都
  • Year and Date: 2012-07-19
• [Presentation] 新しいJulia-Kocienskiオレフィン化試薬の開発, ポスター (2012)
  • Author(s): 河野大喜、瀬見井優、安藤香織
  • Organizer: 日本プロセス化学会2012サマーシンポジウム
  • Place of Presentation: 京都
  • Year and Date: 2012-07-19
• [Presentation] 高E選択的無溶媒HWE反応の開発, ポスター (2012)
  • Author(s): 内田成晃、山田恭平、安藤香織
  • Organizer: 日本プロセス化学会2012サマーシンポジウム
  • Place of Presentation: 京都
  • Year and Date: 2012-07-19
• [Presentation] Development of Z-selective Horner- Wadsworth-Emmons Reagents and the Related Olefin Synthesis (2012)
  • Author(s): Kaori Ando
  • Place of Presentation: Department of Chemistry, University of Iowa, USA
  • Year and Date: 2012-05-08
• [Presentation] 大環状ラクトン合成のための高Ｚ選択的分子内ＨＷＥ反応の開発 (2012)
  • Author(s): 江口勇馬、安藤香織
  • Organizer: 第43回中部地化学関係学協会支部連合秋季大会、名古屋
  • Place of Presentation: 名古屋工業大学
• [Presentation] 大環状ラクトン合成のための高Z選択的分子内HWE反応の開発 (2011)
  • Author(s): 江口勇馬、安藤香織
  • Organizer: 第38回有機典型元素化学討論会
  • Place of Presentation: 金沢
  • Year and Date: 2011-12-08
• [Presentation] HWE反応によるZ-α,β-不飽和ニトリルの合成 (2011)
  • Author(s): 奥村美穂、安藤香織
  • Organizer: 第38回有機典型元素化学討論会
  • Place of Presentation: 金沢
  • Year and Date: 2011-12-08
• [Presentation] ワンポットエステル還元-HWE反応によるZ-α,β-不飽和エステルの合成 (2011)
  • Author(s): 高尾麻美、安藤香織
  • Organizer: 第38回有機典型元素化学討論会
  • Place of Presentation: 金沢
  • Year and Date: 2011-12-08
• [Presentation] リチウムエノラートのアルキル化反応:ミクロ溶媒和モデルを使った理論研究 (2011)
  • Author(s): 安藤香織、諸熊奎治
  • Organizer: 第38回有機典型元素化学討論会
  • Place of Presentation: 金沢
  • Year and Date: 2011-12-08
• [Presentation] HWE反応によるZ-α,β不飽和ニトリルの合成 (2011)
  • Author(s): 奥村美穂、安藤香織
  • Organizer: 第38回有機典型元素化学討論会
  • Place of Presentation: 金沢
  • Year and Date: 2011-12-08
• [Presentation] 無溶媒条件を用いるHWE反応と活性メチレン化合物の選択的モノアルキル化 (2011)
  • Author(s): 足立尚也、米田祥和、山田恭平、安藤香織
  • Organizer: 第38回有機典型元素化学討論会
  • Place of Presentation: 金沢
  • Year and Date: 2011-12-07
• [Presentation] One-pot Preparations of Z-α,β-Unsaturated Esters and Solvent-free HWE Reaction (2011)
  • Author(s): Kaori Ando
  • Organizer: The Seventh International Symposium on Integrated Synthesis
  • Place of Presentation: 神戸(招待講演)
  • Year and Date: 2011-10-09
• [Presentation] Highly E-selective solvent-free Horner-Wadsworth-Emmons reaction catalyzed by DBU (2011)
  • Author(s): 安藤香織、山田恭平
  • Organizer: 第2回日本プロセス化学国際シンポジウム
  • Place of Presentation: 京都
  • Year and Date: 2011-08-12
• [Presentation] Synthesis of Z-α,β- unsaturated esters by one-pot ester reduction and HWE reaction (2011)
  • Author(s): 高尾麻美、安藤香織
  • Organizer: 第2回日本プロセス化学国際シンポジウム
  • Place of Presentation: 京都
  • Year and Date: 2011-08-12
• [Presentation] Highly E-selective solvent-free Homer-Wadsworth-Emmons reaction catalyzed by DBU (2011)
  • Author(s): 安藤香織、山田恭平
  • Organizer: 第2回日本プロセス化学国際シンポジウム
  • Place of Presentation: 京都
  • Year and Date: 2011-08-12
• [Presentation] Selective Monoalkylation of Diethyl Malonate and Related Coumpounds Using Solvent-Free Conditions (2011)
  • Author(s): 足立尚也、米田祥和、安藤香織
  • Organizer: 第2回日本プロセス化学国際シンポジウム
  • Place of Presentation: 京都
  • Year and Date: 2011-08-12
• [Presentation] Synthesis of Z-α,β-unsaturated esters by one-pot ester reduction and HWE reaction (2011)
  • Author(s): 高尾麻美、安藤香織
  • Organizer: 第2回日本プロセス化学国際シンポジウム
  • Place of Presentation: 京都
  • Year and Date: 2011-08-12
• [Presentation] α-チオアレンの2, 5-ジヒドロチオフェンへの金触媒環化反応に関する理論研究 (2011)
  • Author(s): 安藤香織
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜
  • Year and Date: 2011-03-29
• [Presentation] Z選択的分子内HWE反応による大環状化合物の立体選択的合成 (2011)
  • Author(s): 佐藤歌小里、安藤香織
  • Organizer: 日本化学会第91 春季年会
  • Place of Presentation: 横浜
  • Year and Date: 2011-03-28
• [Presentation] Z選択的分子内HWE反応による大環状化合物の立体選択的合成 (2011)
  • Author(s): 佐藤歌小里、安藤香織
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜
  • Year and Date: 2011-03-28
• [Presentation] One-pot Preparations of Z-α,β-Unsaturated Esters and Solvent-free HWE Reaction (2011)
  • Author(s): Kaori Ando
  • Organizer: The Seventh International Symposium on Integrated Synthesis
  • Place of Presentation: Kobe
• [Presentation] Bis(2-t-butylphenyl)phosphonoacetamides for the highly cis-selective synthesis of α,β-unsaturated amides (2010)
  • Author(s): Kaori Ando, Shigeo Nagaya, Yuko Tarumi
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Honolulu, USA
  • Year and Date: 2010-12-18
• [Presentation] Solvent-free Horner- Wadsworth-Emmons reaction using DBU (2010)
  • Author(s): Kyouhei Yamada, Kaori Ando
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Honolulu, USA
  • Year and Date: 2010-12-18
• [Presentation] Bis (2-t-butylphenyl) phosphonoacetamides for the highly cis-selective synthesis of α, β-unsaturated amides' (2010)
  • Author(s): Kaori Ando, Shigeo Nagaya, Yuko Tarumi
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: ホノルル、アメリカ
  • Year and Date: 2010-12-18
• [Presentation] Solvent-free Homer-Wadsworth-Emmons reaction using DBU (2010)
  • Author(s): Kyouhei Yamada, Kaori Ando
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: ホノルル、アメリカ
  • Year and Date: 2010-12-18
• [Presentation] Z-selective intramolecular Horner- Wadsworth-Emmons reaction for the synthesis of macrocylic lactones (2010)
  • Author(s): Kaori Ando, Kenji Narumiya, Hiroaki Takada, Taiji Teruya
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Honolulu, USA
  • Year and Date: 2010-12-15
• [Presentation] Z-selective intramolecular Homer-Wadsworth-Emmons reaction for the synthesis of macrocylic lactones (2010)
  • Author(s): Kaori Ando, Kenji Narumiya, Hiroaki Takada, Taiji Teruya
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: ホノルル、アメリカ
  • Year and Date: 2010-12-15
• [Presentation] Z選択的分子内HWE反応による大環状化合物の立体選択的合成 (2010)
  • Author(s): 佐藤歌小里、成宮健次、高田和宏、照屋太司、安藤香織
  • Organizer: 第27回有機合成化学セミナー
  • Place of Presentation: 舞子
  • Year and Date: 2010-09-03
• [Presentation] Z選択的Horner-Wadsworth-Emmons試薬の開発とその後の展開 (2010)
  • Author(s): 安藤香織
  • Organizer: 第27回有機合成化学セミナー
  • Place of Presentation: 舞子
  • Year and Date: 2010-09-02
• [Presentation] Z選択的Homer-Wadsworth-Emmons試薬の開発とその後の展開 (2010)
  • Author(s): 安藤香織
  • Organizer: 第27回有機合成化学セミナー
  • Place of Presentation: 舞子 招待講演
  • Year and Date: 2010-09-02
• [Presentation] Z-selective Intramolecular Horner- Wadsworth-Emmons Reaction for the Synthesis of Macrocylic Lactones (2010)
  • Author(s): Kaori Ando, Kenji Narumiya, Kazuhiro Takada, Taiji Teruya
  • Organizer: The 21st French-Japanese symposium on medicinal and fine chemistry
  • Place of Presentation: Kyoto
  • Year and Date: 2010-05-10
• [Presentation] Z-selective intramolecular Horner-Wadsworth-Emmons reaction for the synthesis of macrocylic lactones (2010)
  • Author(s): Kaori Ando, Kenji Narumiya, Hiroaki Takada, Taiji Teruya
  • Organizer: The 21^<st> French-Japanese symposium on medicinal and fine chemistry
  • Place of Presentation: 京都
  • Year and Date: 2010-05-10
• [Presentation] Solvent-free Horner-Wadsworth-Emmons反応 (2010)
  • Author(s): 山田恭平、安藤香織
  • Organizer: 第41回中部地化学関係学協会支部連合秋季大会
  • Place of Presentation: 豊橋
• [Presentation] Z選択的分子内HWE反応による大環状化合物の立体選択的合成 (2010)
  • Author(s): 佐藤歌小里、安藤香織
  • Organizer: 第41回中部地化学関係学協会支部連合秋季大会
  • Place of Presentation: 豊橋
• [Presentation] アルコールからZ-α,β-不飽和エステルのワンポット反応 (2010)
  • Author(s): 江上智恵、安藤香織
  • Organizer: 第41回中部地化学関係学協会支部連合秋季大会
  • Place of Presentation: 豊橋
• [Presentation] HWE反応によるE,Z-ジエノエステルの立体選択的合成法の開発 (2010)
  • Author(s): 足立尚也、安藤香織
  • Organizer: 第41回中部地化学関係学協会支部連合秋季大会
  • Place of Presentation: 豊橋
• [Presentation] ワンポット反応を用いるキラルブテノライドの合成 (2010)
  • Author(s): 高尾麻美、安藤香織
  • Organizer: 第41回中部地化学関係学協会支部連合秋季大会
  • Place of Presentation: 豊橋
• [Book] 『使える!有機合成反応 241実践ガイド』(丸岡ら編)、「Z選択的 Horner-Wadsworth-Emmons 反応を活用するZ-α,β-不飽和アミドの合成」 (2010)
  • Author(s): 安藤香織
  • Publisher: 化学同人
• [Book] 『使える!有機合成反応 241実践ガイド』(丸岡ら編)、「Z選択的 Horner-Wadsworth-Emmons 反応を活用するZ-α,β-不飽和ラクトンの合成」 (2010)
  • Author(s): 安藤香織
  • Publisher: 化学同人
• [Book] 『使える!有機合成反応 241実践ガイド』(丸岡ら編)、「高E選択的無溶媒 Horner-Wadsworth-Emmons 反応」 (2010)
  • Author(s): 安藤香織
  • Publisher: 化学同人
• [Book] 使える!有機合成反応241実践ガイド (2010)
  • Author(s): 丸岡啓二, 他137名(安藤香織)
  • Total Pages: 504
  • Publisher: 化学同人
• [Remarks]
  • URL: http://www1.gifu-u.ac.jp/~ando_ap/
• [Remarks]
  • URL: http://www1.gifu-u.ac.jp/~ando_ap/
• [Remarks]
  • URL: http://wwwl.gifu-u.ac.jp/~ando_ap/