{"title":"光霉素i的合成。","authors":"Yuichi Kobayashi, Mohammad Nuruzzaman, Narihito Ogawa, Noriaki Maeda, Kei Miyoshi, Hisato Nonaka, Takumi Murakami","doi":"10.1021/acs.joc.4c02861","DOIUrl":null,"url":null,"abstract":"<p><p>The C5-C11 moiety of phoslactomycin I-i was synthesized via chelation-controlled addition of CH<sub>2</sub>═CHMgBr to the C8 ketone, ozonolysis, and the HWE reaction. The TMS acetylene and C1-C4 were attached to C11 and C5, respectively. A cyclohexyl moiety possessing an iodovinyl group was synthesized from quinic acid. The coupling reaction of the intermediates followed by Zn reduction yielded the <i>cis</i>,<i>cis</i>-diene. Finally, the amino and phosphate groups were attached.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":"3034-3042"},"PeriodicalIF":3.6000,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of Phoslactomycin I-i.\",\"authors\":\"Yuichi Kobayashi, Mohammad Nuruzzaman, Narihito Ogawa, Noriaki Maeda, Kei Miyoshi, Hisato Nonaka, Takumi Murakami\",\"doi\":\"10.1021/acs.joc.4c02861\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>The C5-C11 moiety of phoslactomycin I-i was synthesized via chelation-controlled addition of CH<sub>2</sub>═CHMgBr to the C8 ketone, ozonolysis, and the HWE reaction. The TMS acetylene and C1-C4 were attached to C11 and C5, respectively. A cyclohexyl moiety possessing an iodovinyl group was synthesized from quinic acid. The coupling reaction of the intermediates followed by Zn reduction yielded the <i>cis</i>,<i>cis</i>-diene. Finally, the amino and phosphate groups were attached.</p>\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\" \",\"pages\":\"3034-3042\"},\"PeriodicalIF\":3.6000,\"publicationDate\":\"2025-02-28\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.joc.4c02861\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/2/19 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c02861","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/2/19 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
摘要
phoactomycin i - 1的C5-C11部分是通过螯合控制的CH2 CHMgBr加成到C8酮、臭氧分解和HWE反应合成的。TMS乙炔和C1-C4分别附着在C11和C5上。以奎宁酸为原料合成了含碘乙烯基的环己基。中间体的偶联反应再经过Zn还原得到顺式、顺式二烯。最后，氨基和磷酸基团被连接。
The C5-C11 moiety of phoslactomycin I-i was synthesized via chelation-controlled addition of CH2═CHMgBr to the C8 ketone, ozonolysis, and the HWE reaction. The TMS acetylene and C1-C4 were attached to C11 and C5, respectively. A cyclohexyl moiety possessing an iodovinyl group was synthesized from quinic acid. The coupling reaction of the intermediates followed by Zn reduction yielded the cis,cis-diene. Finally, the amino and phosphate groups were attached.
期刊介绍：
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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