{"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}
引用次数: 0
Abstract
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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