{"title":"肾素和山茶甙的全合成:天然存在的 l-葡萄糖苷的证据","authors":"","doi":"10.1016/j.tetlet.2024.155191","DOIUrl":null,"url":null,"abstract":"<div><p>The first concise synthesis of nepodin-1-<em>O</em>-<em>β</em>-<span>d</span>-glucopyranoside (D-<strong>1</strong>) and its <span>l</span>-glucopyranoside (L-<strong>1</strong>), as well as torachrysone-1-<em>O</em>-<em>β</em>-<span>d</span>-glucopyranoside (D-<strong>2</strong>) and its <span>l</span>-glucopyranoside (L-<strong>2</strong>), was achieved <em>via</em> Fries rearrangement and selective glycosylation. Spectral data, particularly the specific rotation signs of the synthetic <span>l</span>-glucosides, correlated with those of natural products previously isolated from <em>Rumex dentatus</em>. This confirms the presence of naturally occurring <span>l</span>-glucosides, L-<strong>1</strong> and L-<strong>2</strong>, identified through synthetic approaches.</p></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2024-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0040403924002867/pdfft?md5=fcac831db7f019422a172dd0db77982b&pid=1-s2.0-S0040403924002867-main.pdf","citationCount":"0","resultStr":"{\"title\":\"Total synthesis of nepodin and torachrysone glucosides: Evidence for naturally occurring l-glucosides\",\"authors\":\"\",\"doi\":\"10.1016/j.tetlet.2024.155191\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>The first concise synthesis of nepodin-1-<em>O</em>-<em>β</em>-<span>d</span>-glucopyranoside (D-<strong>1</strong>) and its <span>l</span>-glucopyranoside (L-<strong>1</strong>), as well as torachrysone-1-<em>O</em>-<em>β</em>-<span>d</span>-glucopyranoside (D-<strong>2</strong>) and its <span>l</span>-glucopyranoside (L-<strong>2</strong>), was achieved <em>via</em> Fries rearrangement and selective glycosylation. Spectral data, particularly the specific rotation signs of the synthetic <span>l</span>-glucosides, correlated with those of natural products previously isolated from <em>Rumex dentatus</em>. This confirms the presence of naturally occurring <span>l</span>-glucosides, L-<strong>1</strong> and L-<strong>2</strong>, identified through synthetic approaches.</p></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2024-07-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.sciencedirect.com/science/article/pii/S0040403924002867/pdfft?md5=fcac831db7f019422a172dd0db77982b&pid=1-s2.0-S0040403924002867-main.pdf\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403924002867\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924002867","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Total synthesis of nepodin and torachrysone glucosides: Evidence for naturally occurring l-glucosides
The first concise synthesis of nepodin-1-O-β-d-glucopyranoside (D-1) and its l-glucopyranoside (L-1), as well as torachrysone-1-O-β-d-glucopyranoside (D-2) and its l-glucopyranoside (L-2), was achieved via Fries rearrangement and selective glycosylation. Spectral data, particularly the specific rotation signs of the synthetic l-glucosides, correlated with those of natural products previously isolated from Rumex dentatus. This confirms the presence of naturally occurring l-glucosides, L-1 and L-2, identified through synthetic approaches.
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.