帕拉莫内酯 A 的双环丁烯内酯核心的合成：一种生物模拟方法

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2024-08-30 Epub Date: 2024-09-09 DOI:10.1039/d4ob01380h

Grace J. Drummond , Phillip S. Grant , Alisha M. Geurts , Daniel P. Furkert , Margaret A. Brimble

{"title":"帕拉莫内酯 A 的双环丁烯内酯核心的合成：一种生物模拟方法","authors":"Grace J. Drummond , Phillip S. Grant , Alisha M. Geurts , Daniel P. Furkert , Margaret A. Brimble","doi":"10.1039/d4ob01380h","DOIUrl":null,"url":null,"abstract":"<div><div>Pallamolide A is a 7,8-<em>seco</em>-labdane terpenoid possessing a unique bicyclo[2.2.2]octane core and a spiro-butenolide moiety. A biomimetic synthesis of the bicyclic butenolide core over 10 steps is reported, featuring an unexpected autoxidation ring opening, and a vinylogous Mukaiyama aldol reaction which was spontaneously followed by an unusual intramolecular vinylogous aldol reaction to assemble the spiro-butenolide moiety and bicyclic core of pallamolide A.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"22 39","pages":"Pages 8032-8036"},"PeriodicalIF":2.7000,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of the bicyclic butenolide core of pallamolide A: a biomimetic approach†\",\"authors\":\"Grace J. Drummond , Phillip S. Grant , Alisha M. Geurts , Daniel P. Furkert , Margaret A. Brimble\",\"doi\":\"10.1039/d4ob01380h\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Pallamolide A is a 7,8-<em>seco</em>-labdane terpenoid possessing a unique bicyclo[2.2.2]octane core and a spiro-butenolide moiety. A biomimetic synthesis of the bicyclic butenolide core over 10 steps is reported, featuring an unexpected autoxidation ring opening, and a vinylogous Mukaiyama aldol reaction which was spontaneously followed by an unusual intramolecular vinylogous aldol reaction to assemble the spiro-butenolide moiety and bicyclic core of pallamolide A.</div></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"22 39\",\"pages\":\"Pages 8032-8036\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2024-08-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1477052024008000\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/9/9 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052024008000","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/9/9 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

帕拉莫内酯 A 是一种 7,8-seco-labdane萜类化合物，具有独特的双环[2.2.2]辛烷核心和一个螺丁烯内酯分子。本研究报告通过 10 个步骤对双环丁烯内酯核心进行了生物模拟合成，其特点包括意想不到的自氧化开环和乙烯基 Mukaiyama 醛醇反应，该反应之后自发地发生了不寻常的分子内乙烯基醛醇反应，从而组装了帕拉莫内酯 A 的螺丁烯内酯分子和双环核心。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

摘要图片

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

Synthesis of the bicyclic butenolide core of pallamolide A: a biomimetic approach†

Pallamolide A is a 7,8-seco-labdane terpenoid possessing a unique bicyclo[2.2.2]octane core and a spiro-butenolide moiety. A biomimetic synthesis of the bicyclic butenolide core over 10 steps is reported, featuring an unexpected autoxidation ring opening, and a vinylogous Mukaiyama aldol reaction which was spontaneously followed by an unusual intramolecular vinylogous aldol reaction to assemble the spiro-butenolide moiety and bicyclic core of pallamolide A.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.