{"title":"Proposal for structure revision of pinofuranoxin A through total syntheses of stereoisomers","authors":"Kazuki Ujiie, Chiaki Tanaka, Masayoshi Arai, Masaru Hashimoto, Yuki Yoshida, Tomikazu Kawano, Satoru Tamura","doi":"10.1007/s11418-024-01810-5","DOIUrl":null,"url":null,"abstract":"<div><p>The relative configuration of the epoxide functionality in pinofuranoxin A (<b>1</b>), α-alkylidene-β-hydroxy-γ-methyl-γ-butyrolactone with <i>trans</i>-epoxy side chain isolated by Evidente et al. in 2021, was revised by DFT-based spectral reinvestigations and stereo-controlled synthesis. The present investigation demonstrates the difficulty of the configurational elucidation of the stereogenic centers on the conformationally flexible acyclic side-chains. Sharpless’s enantioselective epoxidations and dihydroxylations were quite effective in the reinvestigations of the configurations. As our syntheses made all diastereomers available, these would be quite effective in the next structure-biological activity relationship studies.</p><h3>Graphical Abstract</h3>\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":654,"journal":{"name":"Journal of Natural Medicines","volume":"78 3","pages":"608 - 617"},"PeriodicalIF":2.5000,"publicationDate":"2024-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s11418-024-01810-5.pdf","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Natural Medicines","FirstCategoryId":"3","ListUrlMain":"https://link.springer.com/article/10.1007/s11418-024-01810-5","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0
Abstract
The relative configuration of the epoxide functionality in pinofuranoxin A (1), α-alkylidene-β-hydroxy-γ-methyl-γ-butyrolactone with trans-epoxy side chain isolated by Evidente et al. in 2021, was revised by DFT-based spectral reinvestigations and stereo-controlled synthesis. The present investigation demonstrates the difficulty of the configurational elucidation of the stereogenic centers on the conformationally flexible acyclic side-chains. Sharpless’s enantioselective epoxidations and dihydroxylations were quite effective in the reinvestigations of the configurations. As our syntheses made all diastereomers available, these would be quite effective in the next structure-biological activity relationship studies.
期刊介绍：
The Journal of Natural Medicines is an international journal publishing original research in naturally occurring medicines and their related foods and cosmetics. It covers:
-chemistry of natural products
-biochemistry of medicinal plants
-pharmacology of natural products and herbs, including Kampo formulas and traditional herbs
-botanical anatomy
-cultivation of medicinal plants.
The journal accepts Original Papers, Notes, Rapid Communications and Natural Resource Letters. Reviews and Mini-Reviews are generally invited.
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