Total synthesis of (±)-villosin C and (±)-teuvincenone B
文献类型：期刊论文
| 作者 | Zhou, Jin-Xin1,3; Yan, Ming-Jie2,3; Shi, Xiao-Yu2,3; Wang, Yue-Qi2,3; Shen, Hong-Yan3; Mao, Xu-Dong3; Wang, Jie1,2,3 |
| 刊名 | ORGANIC CHEMISTRY FRONTIERS
 |
| 出版日期 | 2023-11-30 |
| 页码 | 5 |
| ISSN号 | 2052-4129 |
| DOI | 10.1039/d3qo01841e |
| 通讯作者 | Mao, Xu-Dong(maoxd1993@163.com) ; Wang, Jie(jiewang@simm.ac.cn) |
| 英文摘要 | Herein, we report the first total synthesis of 17(15 -> 16)-abeo-abietane diterpenoids (+/-)-villosin C (5) and (+/-)-teuvincenone B (4) in 11 steps. The A/B/C ring system was assembled via a modified three-step sequence on gram-scale, while the D ring was constructed by intramolecular iodoetherification. This synthesis relied largely on the rational design of the order for oxidation state escalation (C6/11/14 -> C7 -> C12 -> C17), which was realized through sequential benzylic iodination/Kornblum oxidation, Siegel-Tomkinson C-H oxidation and iodoetherification. In addition, villosin C (5) and its epimer (5a) were found to have indistinguishable NMR data and the correct configuration for villosin C was elucidated by comparing HPLC trace with a natural sample. Total synthesis of 17(15 -> 16)-abeo-abietane diterpenoids (+/-)-villosin C and (+/-)-teuvincenone B was accomplished for the first time in 11 steps. |
| WOS关键词 | REARRANGED ABIETANE DITERPENOIDS ; CLERODENDRUM-TRICHOTOMUM ; ROOTS ; OXIDATION ; COLEONS ; STEMS |
| 资助项目 | National Outstanding Youth Science Fund Project of National Natural Science Foundation of China[22101290] ; National Natural Science Foundation of China ; Chinese Academy of Sciences ; State Key Laboratory of Chemical Biology, Shanghai Institute of Materia Medica |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| 出版者 | ROYAL SOC CHEMISTRY |
| WOS记录号 | WOS:001113020900001 |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/308125]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Mao, Xu-Dong; Wang, Jie |
| 作者单位 | 1.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 2.Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Chem Biol, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Zhou, Jin-Xin,Yan, Ming-Jie,Shi, Xiao-Yu,et al. Total synthesis of (±)-villosin C and (±)-teuvincenone B[J]. ORGANIC CHEMISTRY FRONTIERS,2023:5. |
| APA | Zhou, Jin-Xin.,Yan, Ming-Jie.,Shi, Xiao-Yu.,Wang, Yue-Qi.,Shen, Hong-Yan.,...&Wang, Jie.(2023).Total synthesis of (±)-villosin C and (±)-teuvincenone B.ORGANIC CHEMISTRY FRONTIERS,5. |
| MLA | Zhou, Jin-Xin,et al."Total synthesis of (±)-villosin C and (±)-teuvincenone B".ORGANIC CHEMISTRY FRONTIERS (2023):5. |
入库方式： OAI收割
来源：上海药物研究所
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