Asymmetric total synthesis of botcinins C, D, and F
Asymmetric total synthesis of botcinins C, D, and F
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DOI：
10.1021/ol801066y
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发表时间：
2008-07-17
期刊：
影响因子：
5.2
通讯作者：
Shiina, Isamu
中科院分区：
文献类型：
--
作者：
Fukui, Hiroki;Shiina, Isamu
肉毒菌素C、D和F的立体选择性全合成是通过不对称Aldol反应、6-Endo环封闭和SML(12)介导的3，4-反式或-顺式分子内立体选择性Reformsky反应有效地实现的。在MNBA和DMAP的作用下，肉毒菌素的主骨架与手性侧链快速酯化生成了肉毒菌素D，这是一种抗稻瘟病病原菌的抗真菌化学物质。
Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.