Total synthesis of (±)-villosin C and (±)-teuvincenone B
文献信息
发布日期
2023-11-30
DOI
10.1039/D3QO01841E
影响因子
5.281
作者
Hong-Yan Shen, Xu-Dong Mao
查看原文
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.
期刊推荐
Crystallography Reports
Russian Journal of Applied Chemistry
Russian Chemical Bulletin
Russian Journal of Organic Chemistry
Current Opinion in Colloid & Interface Science
Acta Materialia
Journal of Natural Medicines
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Russian Journal of General Chemistry
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来源期刊
Organic Chemistry Frontiers
CiteScore:
7.8
自引率:
8.7%
年发文量:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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