Visible-light-mediated site-selective C(sp2)-H alkylation of tropones facilitates semi-synthesis of cephafortunoids A and B
文献类型：期刊论文
| 作者 | Zeng, Qi-Xiang1,2; Zheng, Cheng-Yu2; Ge, Zhan-Peng2; Zhao, Jin-Xin1,2; Yue, Jian-Min1,2
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| 刊名 | CHEMICAL SCIENCE
 |
| 出版日期 | 2025-04-10 |
| 页码 | 9 |
| ISSN号 | 2041-6520 |
| DOI | 10.1039/d5sc01006c |
| 英文摘要 | The synthesis of functionalized tropones constitutes an underexplored chemical space, primarily due to the intrinsic structural properties of the aromatic nucleus. This predicament has impeded extensive investigation into their potential applications in organic and medicinal chemistry. Here, we report a mild and straightforward visible-light-mediated protocol for the alpha-site-selective C(sp2)-H alkylation of tropones, employing unactivated secondary amines as alkylating agents. This method yields up to 89% in 48 examples, and is significantly amenable to late-stage functionalization. The utility is showcased by the effective chemical transformation of fortunolide A into cephafortunoids A and B, representing the first synthetic entry to this unique class of C20Cephalotaxus troponoids. Significantly, this achievement reinforces the chemical feasibility of the newly hypothesized biosynthesis involving direct methylation via radical S-adenosylmethionine (SAM)-dependent methyltransferases. |
| WOS关键词 | NATURAL-PRODUCTS ; DITERPENOIDS ; DIVERSITY ; H-1-NMR |
| 资助项目 | Youth Innovation Promotion Association of the Chinese Academy of Sciences[T2192972] ; Youth Innovation Promotion Association of the Chinese Academy of Sciences[22407131] ; Youth Innovation Promotion Association of the Chinese Academy of Sciences[22237007] ; National Natural Science Foundation of China[2022282] ; Youth Innovation Promotion Association of Chinese Academy of Sciences (CAS)[SIMM0120231001] ; Shanghai Institute of Materia Medica (SIMM) of CAS |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:001468658000001 |
| 出版者 | ROYAL SOC CHEMISTRY |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/317509]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Zhao, Jin-Xin; Yue, Jian-Min |
| 作者单位 | 1.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Zeng, Qi-Xiang,Zheng, Cheng-Yu,Ge, Zhan-Peng,et al. Visible-light-mediated site-selective C(sp2)-H alkylation of tropones facilitates semi-synthesis of cephafortunoids A and B[J]. CHEMICAL SCIENCE,2025:9. |
| APA | Zeng, Qi-Xiang,Zheng, Cheng-Yu,Ge, Zhan-Peng,Zhao, Jin-Xin,&Yue, Jian-Min.(2025).Visible-light-mediated site-selective C(sp2)-H alkylation of tropones facilitates semi-synthesis of cephafortunoids A and B.CHEMICAL SCIENCE,9. |
| MLA | Zeng, Qi-Xiang,et al."Visible-light-mediated site-selective C(sp2)-H alkylation of tropones facilitates semi-synthesis of cephafortunoids A and B".CHEMICAL SCIENCE (2025):9. |
入库方式： OAI收割
来源：上海药物研究所
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