有机催化醌[5 + 2]环加成不对称合成asperone A和B

IF 15.6 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Journal of the American Chemical Society Pub Date : 2025-02-13 DOI:10.1021/jacs.4c1625210.1021/jacs.4c16252

Chunlei Qu, Lu Chen, Peng Wang, Jingwei Zhang, Yiming Ding, Xianwen Long, Tingrong Zhang, Yaqiu Zhao and Jun Deng*,

{"title":"有机催化醌[5 + 2]环加成不对称合成asperone A和B","authors":"Chunlei Qu, Lu Chen, Peng Wang, Jingwei Zhang, Yiming Ding, Xianwen Long, Tingrong Zhang, Yaqiu Zhao and Jun Deng*, ","doi":"10.1021/jacs.4c1625210.1021/jacs.4c16252","DOIUrl":null,"url":null,"abstract":"The first asymmetric total synthesis of the anti-inflammatory polyketides asperones A (1) and B (2) has been accomplished. Key synthetic steps include a Diels–Alder and retro-Diels–Alder cascade to construct the poly substituted phenol, an Al-Salen-catalyzed asymmetric cyanosilylation to form the tertiary alcohol of gregatin A, and an organocatalyzed intermolecular [5 + 2] cycloaddition of p-quinone with electron-deficient alkenes to build the crucial [3.2.1] octane core of asperones A (1) and B (2).","PeriodicalId":49,"journal":{"name":"Journal of the American Chemical Society","volume":"147 8","pages":"6739–6746 6739–6746"},"PeriodicalIF":15.6000,"publicationDate":"2025-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Asymmetric Total synthesis of Asperones A and B through Organocatalyzed Quinone [5 + 2] Cycloaddition\",\"authors\":\"Chunlei Qu, Lu Chen, Peng Wang, Jingwei Zhang, Yiming Ding, Xianwen Long, Tingrong Zhang, Yaqiu Zhao and Jun Deng*, \",\"doi\":\"10.1021/jacs.4c1625210.1021/jacs.4c16252\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The first asymmetric total synthesis of the anti-inflammatory polyketides asperones A (1) and B (2) has been accomplished. Key synthetic steps include a Diels–Alder and retro-Diels–Alder cascade to construct the poly substituted phenol, an Al-Salen-catalyzed asymmetric cyanosilylation to form the tertiary alcohol of gregatin A, and an organocatalyzed intermolecular [5 + 2] cycloaddition of p-quinone with electron-deficient alkenes to build the crucial [3.2.1] octane core of asperones A (1) and B (2).\",\"PeriodicalId\":49,\"journal\":{\"name\":\"Journal of the American Chemical Society\",\"volume\":\"147 8\",\"pages\":\"6739–6746 6739–6746\"},\"PeriodicalIF\":15.6000,\"publicationDate\":\"2025-02-13\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of the American Chemical Society\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/jacs.4c16252\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the American Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/jacs.4c16252","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

摘要

首次完成了抗炎多酮类化合物asperones A(1)和B(2)的不对称全合成。关键的合成步骤包括Diels-Alder级联和反Diels-Alder级联构建多取代苯酚，al - salen催化的不对称氰硅化反应形成gregatin a的叔醇，以及有机催化的对醌与缺电子烯烃的分子间[5 + 2]环加成，构建asperones a(1)和B(2)的关键[3.2.1]辛烷值核心。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Asymmetric Total synthesis of Asperones A and B through Organocatalyzed Quinone [5 + 2] Cycloaddition

查看原文本刊更多论文

Asymmetric Total synthesis of Asperones A and B through Organocatalyzed Quinone [5 + 2] Cycloaddition

The first asymmetric total synthesis of the anti-inflammatory polyketides asperones A (1) and B (2) has been accomplished. Key synthetic steps include a Diels–Alder and retro-Diels–Alder cascade to construct the poly substituted phenol, an Al-Salen-catalyzed asymmetric cyanosilylation to form the tertiary alcohol of gregatin A, and an organocatalyzed intermolecular [5 + 2] cycloaddition of p-quinone with electron-deficient alkenes to build the crucial [3.2.1] octane core of asperones A (1) and B (2).

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

Journal of the American Chemical Society 化学-化学综合

CiteScore

24.40

自引率

6.00%

发文量

2398

审稿时长

1.6 months

期刊介绍： The flagship journal of the American Chemical Society, known as the Journal of the American Chemical Society (JACS), has been a prestigious publication since its establishment in 1879. It holds a preeminent position in the field of chemistry and related interdisciplinary sciences. JACS is committed to disseminating cutting-edge research papers, covering a wide range of topics, and encompasses approximately 19,000 pages of Articles, Communications, and Perspectives annually. With a weekly publication frequency, JACS plays a vital role in advancing the field of chemistry by providing essential research.