E. R. Karimova, L. A. Baltina, T. R. Nugumanov, N. I. Medvedeva, L. V. Spirikhin, O. S. Kukovinets
{"title":"甘草酸甲酯新 A-癸基衍生物的合成","authors":"E. R. Karimova, L. A. Baltina, T. R. Nugumanov, N. I. Medvedeva, L. V. Spirikhin, O. S. Kukovinets","doi":"10.1007/s10600-024-04407-2","DOIUrl":null,"url":null,"abstract":"<p>New A-seco-derivatives of methyl glycyrrhetinate (MeGLC) were synthesized. Cleavage of ring A of the 2-hydroxymethylene-3-oxo-derivative of MeGLC by H<sub>2</sub>O<sub>2</sub> (30%) in the presence of NaOMe (28%) in MeOH led to the 2,3-seco-2,3-diacid, which was isolated as the dimethyl ester. Ozonolysis of the 2-hydroxymethylene-3-oxo-derivative of MeGLC produced for the first time the methyl esters of 2,3-seco-2-ethoxycarbonyl- 18<i>βH</i>-olean-12-ene-2,3,30-trioic acid and 2,3-anhydro-11-oxo-18<i>βH</i>-olean-9,12-diene-2,3,30-trioic acid.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8000,"publicationDate":"2024-08-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of New A-Seco-Derivatives of Methyl Glycyrrhetinate\",\"authors\":\"E. R. Karimova, L. A. Baltina, T. R. Nugumanov, N. I. Medvedeva, L. V. Spirikhin, O. S. Kukovinets\",\"doi\":\"10.1007/s10600-024-04407-2\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>New A-seco-derivatives of methyl glycyrrhetinate (MeGLC) were synthesized. Cleavage of ring A of the 2-hydroxymethylene-3-oxo-derivative of MeGLC by H<sub>2</sub>O<sub>2</sub> (30%) in the presence of NaOMe (28%) in MeOH led to the 2,3-seco-2,3-diacid, which was isolated as the dimethyl ester. Ozonolysis of the 2-hydroxymethylene-3-oxo-derivative of MeGLC produced for the first time the methyl esters of 2,3-seco-2-ethoxycarbonyl- 18<i>βH</i>-olean-12-ene-2,3,30-trioic acid and 2,3-anhydro-11-oxo-18<i>βH</i>-olean-9,12-diene-2,3,30-trioic acid.</p>\",\"PeriodicalId\":514,\"journal\":{\"name\":\"Chemistry of Natural Compounds\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.8000,\"publicationDate\":\"2024-08-06\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemistry of Natural Compounds\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s10600-024-04407-2\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry of Natural Compounds","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s10600-024-04407-2","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Synthesis of New A-Seco-Derivatives of Methyl Glycyrrhetinate
New A-seco-derivatives of methyl glycyrrhetinate (MeGLC) were synthesized. Cleavage of ring A of the 2-hydroxymethylene-3-oxo-derivative of MeGLC by H2O2 (30%) in the presence of NaOMe (28%) in MeOH led to the 2,3-seco-2,3-diacid, which was isolated as the dimethyl ester. Ozonolysis of the 2-hydroxymethylene-3-oxo-derivative of MeGLC produced for the first time the methyl esters of 2,3-seco-2-ethoxycarbonyl- 18βH-olean-12-ene-2,3,30-trioic acid and 2,3-anhydro-11-oxo-18βH-olean-9,12-diene-2,3,30-trioic acid.
期刊介绍:
Chemistry of Natural Compounds publishes reviews and general articles about the structure of different classes of natural compounds, the chemical characteristics of botanical families, genus, and species, to establish the comparative laws and connection between physiological activity and the structure of substances.