{"title":"Total Synthesis and Determination of the Absolute Configuration of Shodoamide C: An Amphotericin B Potentiator against Candida albicans","authors":"Shogo Ueki, Akihiro Hirata, Akiho Yagi, Masahiro Iwahori, Hiroshi Tomoda, Ryuji Uchida, Tohru Nagamitsu, Masaki Ohtawa","doi":"10.1021/acs.orglett.5c01017","DOIUrl":null,"url":null,"abstract":"The total synthesis and structural determination of shodoamide C (<b>1</b>), a compound that enhances the activity of amphotericin B against <i>Candida albicans</i>, have been achieved. A synthetic strategy for compound <b>1</b> facilitated the efficient synthesis of all 16 stereoisomers, allowing for the identification of the four previously unknown stereocenters of <b>1</b> through the chiral recycle HPLC analyses. All stereoisomers of <b>1</b> showed similar activity, indicating that their stereochemistries minimally influenced it.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"18 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c01017","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
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Abstract
The total synthesis and structural determination of shodoamide C (1), a compound that enhances the activity of amphotericin B against Candida albicans, have been achieved. A synthetic strategy for compound 1 facilitated the efficient synthesis of all 16 stereoisomers, allowing for the identification of the four previously unknown stereocenters of 1 through the chiral recycle HPLC analyses. All stereoisomers of 1 showed similar activity, indicating that their stereochemistries minimally influenced it.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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