{"title":"Steroidal sapogenin-derived chirons: underdeveloped building blocks with methyl-branched chiral centers","authors":"Yu-Chuan Pu, Gen-Ying Liu, Ran Gao, Cheng-Yu He","doi":"10.1039/d5qo00090d","DOIUrl":null,"url":null,"abstract":"Three kinds of chiral lactones with methyl-branched stereocenters could be obtained on large scale based on H2O2-mediated oxidative degradation of steroidal sapogenins. These chiral lactones are valuable chirons for the total synthesis of bioactive compounds containing methyl-branched chiral centers. This review summarizes comprehensively the synthetic application of the steroidal sapogenin-derived chiral lactones in insect pheromones, natural products and pharmaceuticals, with a particular focus on the chirality transfer from chiral lactones to the corresponding motifs of target molecules. We hope these underdeveloped chirons can act as a complement to commonly used methyl-branched chirons such as citronellol, Roche ester, and meet more synthetic application in the future.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"49 1","pages":""},"PeriodicalIF":4.6000,"publicationDate":"2025-03-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5qo00090d","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
Three kinds of chiral lactones with methyl-branched stereocenters could be obtained on large scale based on H2O2-mediated oxidative degradation of steroidal sapogenins. These chiral lactones are valuable chirons for the total synthesis of bioactive compounds containing methyl-branched chiral centers. This review summarizes comprehensively the synthetic application of the steroidal sapogenin-derived chiral lactones in insect pheromones, natural products and pharmaceuticals, with a particular focus on the chirality transfer from chiral lactones to the corresponding motifs of target molecules. We hope these underdeveloped chirons can act as a complement to commonly used methyl-branched chirons such as citronellol, Roche ester, and meet more synthetic application in the future.
期刊介绍：
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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