Boronic Acid-Catalyzed Final-Stage Site-Selective Acylation for the Total Syntheses of <i>O</i>-3′-Acyl Bisabolol β-D-Fucopyranoside Natural Products and Their Analogues
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- Nakamura Yuki
- Laboratory of Organic Chemistry for Drug Development and Research Laboratories, Department of Pharmaceutical Sciences, Kitasato University
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- Ochiai Takayuki
- Laboratory of Organic Chemistry for Drug Development and Research Laboratories, Department of Pharmaceutical Sciences, Kitasato University
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- Makino Kazuishi
- Laboratory of Organic Chemistry for Drug Development and Research Laboratories, Department of Pharmaceutical Sciences, Kitasato University
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- Shimada Naoyuki
- Laboratory of Organic Chemistry for Drug Development and Research Laboratories, Department of Pharmaceutical Sciences, Kitasato University
Bibliographic Information
- Other Title
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- Boronic Acid-Catalyzed Final-Stage Site-Selective Acylation for the Total Syntheses of O-3'-Acyl Bisabolol β-D-Fucopyranoside Natural Products and Their Analogues
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Description
<p>The first concise total syntheses of O-3′-senecioyl α-bisabolol β-D-fucopyranoside (4a) and O-3′-isovaleroyl α-bisabolol β-D-fucopyranoside (4b) were achieved through final-stage site-selective acylation via the activation of cis-vicinal diols by imidazole-containing boronic acid catalysts as a key step. This synthetic method was also effective for the syntheses of unnatural analogues with modified acyl side chains or carbohydrate moiety.</p>
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 69 (3), 281-285, 2021-03-01
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390850247500196480
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- NII Article ID
- 130007993055
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- NII Book ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 031308990
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- PubMed
- 33642477
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
- KAKEN
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- Abstract License Flag
- Disallowed