Organic chemistry using acetal-type salt species
Project/Area Number |
18K06576
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Research Category |
Grant-in-Aid for Scientific Research (C)
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Allocation Type | Multi-year Fund |
Section | 一般 |
Review Section |
Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
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Research Institution | Osaka University |
Principal Investigator |
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Co-Investigator(Kenkyū-buntansha) |
滝澤 忍 大阪大学, 産業科学研究所, 准教授 (50324851)
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Project Period (FY) |
2018-04-01 – 2022-03-31
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Project Status |
Completed (Fiscal Year 2021)
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Budget Amount *help |
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2020: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2019: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2018: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
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Keywords | 塩化学種 / アセタール / 脱保護 / in situ protection法 / 反応性の逆転 / 環状エーテル / amphidinolide C / ホスホニウム塩 / アンフィジノリドC / 不斉ジヒドロキシ化 / 光学活性THF環 / 不斉酸化 / AD-mix-β / アセタール型塩化学種 / 芳香族MOM-エーテル / ホスホニウム塩化学種 / α,β-不飽和アルデヒド / α,β-不飽和エステル / α,β-不飽和アミド / ピリジニウム型塩化学種 / 官能基選択的脱アセタール化 / エノン / 環状エーテル化合物 / アセタール型ピリジニウム塩 / アセタール型ホスホニウム塩 / 含フッ素化合物 |
Outline of Final Research Achievements |
The true active species for pyridinium-type salt chemical species formation from acetals proved to be a bulky complex consisting of TMSOTf and a pyridine base. Next, we succeeded in the selective deprotection of acetals. In addition, we were able to develop a deprotection method for acetal, which has the opposite reactivity to the conventional method. We also succeeded in the conversion reaction of enone in the presence of α,β-unsaturated aldehyde and the conversion of α,β-unsaturated Weinrebamide in the presence of α,β-unsaturated ester. In addition, we succeeded in a practical one-pot asymmetric synthesis of ether ring using the in situ protection method from an acyclic compound containing both α,β-unsaturated aldehyde and α,β-unsaturated ester. This method was applied concise synthesis of amphidinolide C.
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Academic Significance and Societal Importance of the Research Achievements |
申請者のアセタールの脱保護は、弱塩基性条件下で進行するユニークなものである。また従来法と逆の反応性を示すため、従来法では共存できない官能基も共存できるため、我々の手法の拡大は大きな意義がある。 またin situ protection法を用いると、高反応性の官能基の保護・脱保護の過程が不要であるため、これまでにも様々な手法が開発されているが、それらは厳密な反応制御が必要である等の問題を残していた。申請者の手法は厳密な反応制御が不要で、かつ市販の試薬を用いるため、非常に実用性の高いものである。さらに環状エーテル合成法は非常に効率が良い手法であり、含エーテル環天然物の合成に威力を発揮する。
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Report
(5 results)
Research Products
(60 results)
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[Journal Article] Discovery and structure-activity relationship of imidazolinylindole derivatives as kallikrein 7 inhibitors2019
Author(s)
Murafuji, Hidenobu; Muto, Tsuyoshi; Goto, Megumi; Imajo, Seiichi; Sugawara, Hajime; Oyama, Yoshiaki; Minamitsuji, Yutaka; Miyazaki, Shuji; Murai, Kenichi; Fujioka, Hiromichi
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Journal Title
Bioorganic & Medicinal Chemistry Letters
Volume: 29
Issue: 2
Pages: 334-338
DOI
Related Report
Peer Reviewed
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[Journal Article] Direct Synthesis of Dialkylaryl-vinylsilane Derivatives: Metathesis of Dialkylaryl-iso-propenylsilane and Its Application to Tetracyclic Silacycle Dye Synthesis2019
Author(s)
Shohei Yoshioka, Tsunayoshi Takehara, Tsuyoshi Matsuzaki, Takeyuki Suzuki, Hirofumi Tsujino, Tadayuki Uno, Yasuo Tsutsumi, Kenichi Murai, Hiromichi Fujioka, Mitsuhiro Arisawa
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Journal Title
Chemical Communications,
Volume: 55
Issue: 93
Pages: 14070-14073
DOI
Related Report
Peer Reviewed
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[Journal Article] Highly Discriminative and Chemoselective Deprotection/Transformations of Acetals with the Combination of Trialkylsilyl Triflate/2,4,6-Collidine2018
Author(s)
Reiya Ohta, Nao Matsumoto, Yoshifumi Ueyama, Yuichi Kuboki, Hiroshi Aoyama, Kenichi Murai, Mitsuhiro Arisawa, Tomohiro Maegawa, Hiromichi Fujioka
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Journal Title
JOURNAL OF ORGANIC CHEMISTRY
Volume: 83
Issue: 12
Pages: 6432-6443
DOI
Related Report
Peer Reviewed / Int'l Joint Research
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[Journal Article] Reusable Immobilized Iron(II) Nanoparticle Pre-Catalysts for Ligand-Free Kumada Coupling2018
Author(s)
Toshiki Akiyama, Yuki Wada, Kellie Jenkinson, Tetsuo Honma, Kazuki Tsuruta, Yusuke Tamenori, Hitoshi Haneoka, Tsunayoshi Takehara, Takeyuki Suzuki, Kenichi Murai, Hiromichi Fujioka, Yoshihiro Sato, Andrew E. H. Wheatley, Mitsuhiro Arisawa
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Journal Title
Acs Applied Nano Materials
Volume: 1
Issue: 12
Pages: 6950-6958
DOI
Related Report
Peer Reviewed / Int'l Joint Research
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