{"title":"(±)-de-O-methyllasiodiplodin 的高效合成","authors":"","doi":"10.1016/j.tetlet.2024.155184","DOIUrl":null,"url":null,"abstract":"<div><p>Resorcinolic macrolides are a large class of fungal natural products with conserved resorcinolic ester cores within highly variable ten- to fourteen-membered macrocycles. They exhibit a broad range of biological activities, depending largely on the size and substitution on the macrocycle bridge. Here, we report a protecting group-free synthesis of <span><math><mrow><mo>(</mo><mo>±</mo><mo>)</mo></mrow></math></span>-de-<em>O</em>-methyllasiodiplodin, a minimal resorcinolic macrolide derived from the fungus <em>Lasiodiplodia theobromae</em>. The route proceeds in 42% yield over 5 steps (longest linear sequence) from 9-decenoic acid, a cheap and abundant starting material. Given the broad commercial availability of a variety of similar (terminal)-enoic acids, this route provides an entry to libraries of resorcinolic macrolides with highly variable macrocycle bridges.</p></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Efficient synthesis of (±)-de-O-methyllasiodiplodin\",\"authors\":\"\",\"doi\":\"10.1016/j.tetlet.2024.155184\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Resorcinolic macrolides are a large class of fungal natural products with conserved resorcinolic ester cores within highly variable ten- to fourteen-membered macrocycles. They exhibit a broad range of biological activities, depending largely on the size and substitution on the macrocycle bridge. Here, we report a protecting group-free synthesis of <span><math><mrow><mo>(</mo><mo>±</mo><mo>)</mo></mrow></math></span>-de-<em>O</em>-methyllasiodiplodin, a minimal resorcinolic macrolide derived from the fungus <em>Lasiodiplodia theobromae</em>. The route proceeds in 42% yield over 5 steps (longest linear sequence) from 9-decenoic acid, a cheap and abundant starting material. Given the broad commercial availability of a variety of similar (terminal)-enoic acids, this route provides an entry to libraries of resorcinolic macrolides with highly variable macrocycle bridges.</p></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2024-07-18\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S004040392400279X\",\"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/S004040392400279X","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Efficient synthesis of (±)-de-O-methyllasiodiplodin
Resorcinolic macrolides are a large class of fungal natural products with conserved resorcinolic ester cores within highly variable ten- to fourteen-membered macrocycles. They exhibit a broad range of biological activities, depending largely on the size and substitution on the macrocycle bridge. Here, we report a protecting group-free synthesis of -de-O-methyllasiodiplodin, a minimal resorcinolic macrolide derived from the fungus Lasiodiplodia theobromae. The route proceeds in 42% yield over 5 steps (longest linear sequence) from 9-decenoic acid, a cheap and abundant starting material. Given the broad commercial availability of a variety of similar (terminal)-enoic acids, this route provides an entry to libraries of resorcinolic macrolides with highly variable macrocycle bridges.
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.