{"title":"Total Syntheses of (+)-Aigialospirol and (+)-7′,8′-Dihydroaigialospirol by a One-Pot Stepwise Approach","authors":"Atsushi Nakayama, Hidemitsu Yamanaka, Rika Yamasaki, Naoki Hashimoto, Tetsuro Shinada","doi":"10.1021/acs.orglett.5c00484","DOIUrl":null,"url":null,"abstract":"(+)-Aigialospirol and (+)-7′,8′-dihydroaigialospirol are known to be spiroketal polyketide-type natural products isolated from mangrove-derived fungus <i>Aigialus parvus</i> BCC 5311. These polyketides are structurally characterized by fusing resorcylic acid lactone and spiroketal moieties containing six asymmetric carbon centers. In this paper, we describe concise and stereoselective syntheses of these natural products based on biosynthesis-inspired transformation in nine steps. The total syntheses are highlighted by a one-pot stepwise synthesis involving (i) stereoselective lactone ring formation from a chiral epoxide, (ii) reduction of alkyne, (iii) global deprotection, and (iv) spiroketal formation, which are performed in the final step of the total synthesis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"37 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-03-20","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.5c00484","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
(+)-Aigialospirol and (+)-7′,8′-dihydroaigialospirol are known to be spiroketal polyketide-type natural products isolated from mangrove-derived fungus Aigialus parvus BCC 5311. These polyketides are structurally characterized by fusing resorcylic acid lactone and spiroketal moieties containing six asymmetric carbon centers. In this paper, we describe concise and stereoselective syntheses of these natural products based on biosynthesis-inspired transformation in nine steps. The total syntheses are highlighted by a one-pot stepwise synthesis involving (i) stereoselective lactone ring formation from a chiral epoxide, (ii) reduction of alkyne, (iii) global deprotection, and (iv) spiroketal formation, which are performed in the final step of the total synthesis.
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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