Concise synthesis of amino acid component of amicoumacins via dihydrooxazine formation through intramolecular conjugate addition
Amicoumacins are a family of antibiotics with a variety of important bioactivities. A concise and efficient method was developed for synthesizing the amino acid component of amicoumacins via the corresponding dihydrooxazine intermediate. The dihydrooxazine ring was formed with complete stereoselecti...
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| Veröffentlicht in: | Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2023-01, Vol.87 (2), p.131-137 |
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| container_end_page | 137 |
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| container_issue | 2 |
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| container_title | Bioscience, biotechnology, and biochemistry |
| container_volume | 87 |
| creator | Matsushima, Yoshitaka Ogawa, Yukako Nishi, Katsuya Nakata, Kyosuke |
| description | Amicoumacins are a family of antibiotics with a variety of important bioactivities. A concise and efficient method was developed for synthesizing the amino acid component of amicoumacins via the corresponding dihydrooxazine intermediate. The dihydrooxazine ring was formed with complete stereoselectivity through an intramolecular conjugate addition of a δ-trichloroacetimidoyloxy-α,β-unsaturated ester, which was obtained from a known 4,6-O-p-methoxybenzylidene-protected d-glucose. The synthesis developed in this study can be used to synthesize the building blocks of amicoumacins and can likely be adapted for the synthesis of other types of molecules possessing dihydrooxazine rings or amino alcohol moieties. |
| doi_str_mv | 10.1093/bbb/zbac182 |
| format | Article |
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A concise and efficient method was developed for synthesizing the amino acid component of amicoumacins via the corresponding dihydrooxazine intermediate. The dihydrooxazine ring was formed with complete stereoselectivity through an intramolecular conjugate addition of a δ-trichloroacetimidoyloxy-α,β-unsaturated ester, which was obtained from a known 4,6-O-p-methoxybenzylidene-protected d-glucose. 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| ispartof | Bioscience, biotechnology, and biochemistry, 2023-01, Vol.87 (2), p.131-137 |
| issn | 1347-6947 1347-6947 |
| language | eng |
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| source | MEDLINE; Oxford University Press Journals All Titles (1996-Current) |
| subjects | Amino Acids Anti-Bacterial Agents Cyclization Esters - chemistry |
| title | Concise synthesis of amino acid component of amicoumacins via dihydrooxazine formation through intramolecular conjugate addition |
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