{"title":"灵芝经皮化合物 (±)-spiroapplanatumine O 和 (±)-applanatumol B/W 的合成","authors":"","doi":"10.1016/j.tetlet.2024.155192","DOIUrl":null,"url":null,"abstract":"<div><p>Total synthesis of (±)-applanatumol W, formal syntheses of (±)-spiroapplanatumine O and (±)-applanatumol B were accomplished using a common intermediate, methyl benzoyl cyclopentane carboxylate <strong>9</strong>. This intermediate was synthesized through a one-pot reaction involving formation of Michael acceptor cyclopentenone through first Michael addition of malonate to acrolein, Aldol condensation and dehydration, followed by Michael addition of allylcuprate and subsequent demethoxycarboxylation.</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":"","citationCount":"0","resultStr":"{\"title\":\"Syntheses of Ganoderma meroterpenoids (±)-spiroapplanatumine O and (±)-applanatumol B/W\",\"authors\":\"\",\"doi\":\"10.1016/j.tetlet.2024.155192\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Total synthesis of (±)-applanatumol W, formal syntheses of (±)-spiroapplanatumine O and (±)-applanatumol B were accomplished using a common intermediate, methyl benzoyl cyclopentane carboxylate <strong>9</strong>. This intermediate was synthesized through a one-pot reaction involving formation of Michael acceptor cyclopentenone through first Michael addition of malonate to acrolein, Aldol condensation and dehydration, followed by Michael addition of allylcuprate and subsequent demethoxycarboxylation.</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\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403924002879\",\"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/S0040403924002879","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
摘要
(±)-applanatumol W 的全合成、(±)-spiroapplanatumine O 和 (±)-applanatumol B 的正式合成都是使用一种常见的中间体--甲基苯甲酰环戊烷羧酸酯 9 来完成的。这种中间体是通过单锅反应合成的,其中包括首先通过丙二酸与丙烯醛的迈克尔加成反应、醛缩合和脱水形成迈克尔受体环戊烯酮,然后通过烯丙基硫酸酯的迈克尔加成反应和随后的脱甲氧基羧化反应。
Syntheses of Ganoderma meroterpenoids (±)-spiroapplanatumine O and (±)-applanatumol B/W
Total synthesis of (±)-applanatumol W, formal syntheses of (±)-spiroapplanatumine O and (±)-applanatumol B were accomplished using a common intermediate, methyl benzoyl cyclopentane carboxylate 9. This intermediate was synthesized through a one-pot reaction involving formation of Michael acceptor cyclopentenone through first Michael addition of malonate to acrolein, Aldol condensation and dehydration, followed by Michael addition of allylcuprate and subsequent demethoxycarboxylation.
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.