Selective Transformations Using Organoboron Catalysis
| Project/Area Number |
16K18850
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Chemical pharmacy
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| Research Institution | Kitasato University |
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Principal Investigator |
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| Project Period (FY) |
2016-04-01 – 2019-03-31
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| Project Status |
Completed (Fiscal Year 2018)
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| Budget Amount *help |
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2018: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2017: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
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| Keywords | ホウ素 / ボロン酸 / アミド化 / アシル化 / 官能基化 / 位置選択性 / 糖 / 有機触媒 / 化学選択性 / 触媒 / 有機ホウ素触媒 / 官能基選択性 / ヒドロキシカルボン酸 / ジペプチド / 無保護糖 / グリコシル化 / ヒドロキシ基 / カルボン酸 / 活性化 / 糖鎖合成 / 脱水縮合 / ペプチド / 有機合成 |
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| Outline of Final Research Achievements |
The direct catalytic dehydrative amidation of β-hydroxycarboxylic acids with amines was developed. A biphenyl-based diboronic acid anhydride possessing a B-O-B skeleton was shown to be an exceptionally effective catalyst for the reaction, providing β-hydroxycarboxylic amides in high to excellent yields with low catalyst loading, in the absence of additives or dehydration protocols. The present protocol could be applied to the one-step drug synthesis.
Site-selective acylation of unprotected carbohydrates by using stable, storable, and easily handled imidazole-containing organoboronic acid catalysts was also developed. This catalytic process with low catalyst loading enabled the introduction of a wide variety of acyl functional groups into the equatorial position of cis-vicinal diols in unprotected hexapyranosides with excellent site-selectivity. The present protocol could be applied to the synthesis of natural products by using as final-stage functionalization.
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| Academic Significance and Societal Importance of the Research Achievements |
本研究で見出されたジボロン酸無水物触媒反応により、カルボン酸とアミンから効率的にアミドを合成することが可能となった。アミドは多くの医薬品構造中に含まれる化学結合様式であることから、本研究は創薬に寄与することが期待される。
本研究で見出されたボロン酸触媒反応により、従来法と比較して糖質関連化合物の合成を簡略化することができた。これにより、多くの生命現象の解明に必要不可欠な糖質関連化合物の量的供給に寄与することが期待される。
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Report
(4 results)
Research Products
(18 results)
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[Journal Article] Deprotection of silyl ethers by using SO3H silica gel: Application to sugar, nucleoside, and alkaloid derivatives2017
Author(s)
Hideaki Fujii, Naoyuki Shimada, Masaki Ohtawa, Fumika Karaki, Masayoshi Koshizuka, Kohei Hayashida, Mitsuhiro Kamimura, Kazuishi Makino, Tohru Nagamitsu, Hiroshi Nagase
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Journal Title
Tetrahedron
Volume: 73
Issue: 36
Pages: 5425-5429
DOI
Related Report
Peer Reviewed
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