Enantioselective total syntheses of bioactive natural products via the enolate intermediate with dynamic chirality
| Project/Area Number |
26460006
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Kanazawa University (2015-2016)
Kyoto University (2014) |
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Principal Investigator |
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2016: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2014: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
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| Keywords | 天然物全合成 / 不斉合成 / 不斉記憶 / キラルエノラート / ＮＨＣカルベン触媒 / 不斉アルドール反応 / 不斉反応 / α－アリール化 / 全合成 |
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| Outline of Final Research Achievements |
Enantioselective total syntheses of bioactive natural products were carried out. 1) Metachromin J and K, 2) epiliolide and its hydrate, and 3) altemicidin were chosen as target molecules because of their unique bioacitivites. In metachromin derivative synthesis, the precursor for asymmetric reaction via C-O axially chiral enolate was invesitigated. The preparation of substrate for synthesizing epiliolides through intramolecular cyclization using NHC catalyst and asymmetric aldol reaction has been accomplished. Investigation of alpha-arylation reaciton with C-N axially chiral enolate and benzyne, which is supposed as key reaction in altemicidin synthesis, resulted in giving benzocyclobutenone derivative bearing tetrasubstituted carbon in high enantioselectivity.
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Report
(4 results)
Research Products
(22 results)
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[Journal Article] α-Arylation of α-Amino Acid Derivatives with Arynes via Memory of Chirality: Asymmetric Synthesis of Benzocy-clobutenones with Tetrasubstituted Carbon2017
Author(s)
Kasamatsu, K., Yoshimura, T., Mandi, A., Taniguchi, T., Monde, K., Furuta, T., Kawabata, T.
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Journal Title
Org. Lett.
Volume: 19
Issue: 2
Pages: 352-355
DOI
Related Report
Peer Reviewed
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