Concise synthesis of amino acid component of amicoumacins via dihydrooxazine formation through intramolecular conjugate addition
Concise synthesis of amino acid component of amicoumacins via dihydrooxazine formation through intramolecular conjugate addition
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DOI：
10.1093/bbb/zbac182
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发表时间：
2022-11-23
影响因子：
1.6
通讯作者：
Nakata，Kyosuke
中科院分区：
文献类型：
--
作者：
Matsushima，Yoshitaka;Ogawa，Yukako;Nakata，Kyosuke
Amicoumacins是一类具有多种重要生物活性的抗生素。以二氢恶嗪为中间体，建立了一种简便、高效的氨基香豆素类化合物氨基酸组分的合成方法。从已知的4，6-O-对甲氧基亚苄基保护的d-葡萄糖得到δ-三氯乙酰亚胺基氧基-α，β-不饱和酯，通过分子内共轭加成反应，完全立体选择性地形成二氢恶嗪环。本研究中开发的合成方法可用于合成amicoumacins的结构单元，并可能适用于合成具有二氢恶嗪环或氨基醇部分的其他类型的分子。
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-protectedd-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.