Home

Citation: Yanguang Wang, Ping Lu. Total Synthesis of Capitulactone: Analysis of Problem 9 of the 54th International Chemistry Olympiad[J]. University Chemistry, ;2022, 37(12): 220905. doi: 10.3866/PKU.DXHX202209052 shu

Total Synthesis of Capitulactone: Analysis of Problem 9 of the 54th International Chemistry Olympiad

Yanguang Wang ^, ,
Ping Lu

Department of Chemistry, Zhejiang University, Hangzhou 310027, China

Corresponding author: Yanguang Wang, orgwyg@zju.edu.cn
Received Date: 20 September 2022

The problem 9 of the 54th International Chemistry Olympiad describes the total synthesis of capitulactone which was isolated from a plant called Curculigo capitulate, a Chinese medicinal herb. Isolation and synthesis of Capitulactone were reported by academician Jian-Min Yue of Shanghai Institute of Materia Medica in 2019. This problem comprises of two parts. The first part is the construction of the skeleton of this natural product, and the second part is the introduction of the stereocenter derived from chiral pool D-mannitol. The interesting thing is that the oxidative cleavage of the protected D-mannitol leads to a single chiral product, and the stereocenter remains neatly during all transformations. The fundamental knowledges examined in this problem include a number of classical organic reactions like electrophilic substitution, nucleophilic substitution, oxidation, reduction, cleavage of ester bond, ring-opening of epoxides, and formation of ketals. Furthermore, protection and deprotection of hydroxyl groups are also involved in this problem.
- Capitulactone,
- Natural products,
- Total synthesis,
- Chinese medicinal herbal
1. [1]
  Li, S.; Yu, J.-H.; Fan, Y.-Y.; Liu, Q.-F.; Li, Z.-C.; Xie, Z.-X.; Li, Y.; Yue, J.-M. J. Org. Chem. 2019, 84, 5195.
2. [2]
  ]. www.icho2022.cn
3. [3]
  Xu, Y.; Prestwich, G. D. J. Org. Chem. 2002, 67, 7158.
4. [4]
  Leyes, A. E.; Poulter, C. D. Org. Lett. 1999, 1, 1067.
5. [5]
  Baldwin, J. J.; Raab, A. W.; Mensler, K.; Arison, B. H.; McClure, D. E. J. Org. Chem. 1978, 43, 4876.
6. [6]
  Debost, J.-L.; Gelas, J.; Horton. D. J. Org. Chem. 1983, 48, 1381.
1. [1]
  Tao Yang , Kaijiao Duan , Siyu Li , Jing Wei , Qingdi Yang , Qian Wang . A Comprehensive and Innovative Chemical Experimental Teaching: Extraction and Identification of Tea Polyphenols from Pu'er Tea and the Application in Hand Cream Making. University Chemistry, 2024, 39(8): 270-275. doi: 10.3866/PKU.DXHX202312040
2. [2]
  Lijuan Wang , Yuping Ning , Jian Li , Sha Luo , Xiongfei Luo , Ruiwen Wang . Enhancing the Advanced Nature of Natural Product Chemistry Laboratory Courses with New Research Findings: A Case Study of the Application of Berberine Hydrochloride in Photodynamic Antimicrobial Films. University Chemistry, 2024, 39(11): 241-250. doi: 10.12461/PKU.DXHX202403017
3. [3]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
4. [4]
  Zhuomin Zhang , Lanrui Yang , Baorong Zhang , Gongke Li . 化学分析全英课程思政建设初探. University Chemistry, 2025, 40(8): 58-65. doi: 10.12461/PKU.DXHX202410010
5. [5]
  Zhonghong Yan , Chunxia Li , Ruolin Yang . Analysis of the Use and Effectiveness of Concept Mapping Assignments in English Medium Instruction of General Chemistry. University Chemistry, 2025, 40(4): 224-231. doi: 10.12461/PKU.DXHX202405138
6. [6]
  Weizhi Wang , Jieling Qin , Jie Cao . 仪器分析全英语课程设置的必要性与思政教育实践融合. University Chemistry, 2025, 40(8): 117-123. doi: 10.12461/PKU.DXHX202410067
7. [7]
  Peihong Fan , Hongxiang Lou . 研究生高等天然药物化学课程的教学改革探索——导学互促式混合课堂教学与自主学习能力培养. University Chemistry, 2025, 40(6): 16-21. doi: 10.12461/PKU.DXHX202407078
8. [8]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
9. [9]
  Jiahui YU , Jixian DONG , Yutong ZHAO , Fuping ZHAO , Bo GE , Xipeng PU , Dafeng ZHANG . The morphology control and full-spectrum photodegradation tetracycline performance of microwave-hydrothermal synthesized BiVO₄:Yb³⁺,Er³⁺ photocatalyst. Journal of Fuel Chemistry and Technology, 2025, 53(3): 348-359. doi: 10.1016/S1872-5813(24)60514-1
10. [10]
  Hui Wang , Yiwen Zhang , Dong Liu . “三全育人”理念下培养应用型创新人才——以“赛教结合”模式为例的探索与实践. University Chemistry, 2025, 40(6): 37-42. doi: 10.12461/PKU.DXHX202407091
11. [11]
  Xingchao Zhao , Xiaoming Li , Ming Liu , Zijin Zhao , Kaixuan Yang , Pengtian Liu , Haolan Zhang , Jintai Li , Xiaoling Ma , Qi Yao , Yanming Sun , Fujun Zhang . Photomultiplication-Type All-Polymer Photodetectors and Their Applications in Photoplethysmography Sensor. Acta Physico-Chimica Sinica, 2025, 41(1): 100007-0. doi: 10.3866/PKU.WHXB202311021
12. [12]
  Xue Dong , Xiaofu Sun , Shuaiqiang Jia , Shitao Han , Dawei Zhou , Ting Yao , Min Wang , Minghui Fang , Haihong Wu , Buxing Han . Electrochemical CO₂ Reduction to C₂₊ Products with Ampere-Level Current on Carbon-Modified Copper Catalysts. Acta Physico-Chimica Sinica, 2025, 41(3): 2404012-0. doi: 10.3866/PKU.WHXB202404012
13. [13]
  Haoyu Sun , Dun Li , Yuanyuan Min , Yingying Wang , Yanyun Ma , Yiqun Zheng , Hongwen Huang . Hierarchical Palladium-Copper-Silver Porous Nanoflowers as Efficient Electrocatalysts for CO₂ Reduction to C₂₊ Products. Acta Physico-Chimica Sinica, 2024, 40(6): 2307007-0. doi: 10.3866/PKU.WHXB202307007
14. [14]
  Xudong Lv , Tao Shao , Junyan Liu , Meng Ye , Shengwei Liu . Paired Electrochemical CO₂ Reduction and HCHO Oxidation for the Cost-Effective Production of Value-Added Chemicals. Acta Physico-Chimica Sinica, 2024, 40(5): 2305028-0. doi: 10.3866/PKU.WHXB202305028
15. [15]
  Yuchen Zhou , Huanmin Liu , Hongxing Li , Xinyu Song , Yonghua Tang , Peng Zhou . Designing thermodynamically stable noble metal single-atom photocatalysts for highly efficient non-oxidative conversion of ethanol into high-purity hydrogen and value-added acetaldehyde. Acta Physico-Chimica Sinica, 2025, 41(6): 100067-0. doi: 10.1016/j.actphy.2025.100067
16. [16]
  Hui-Ying Chen , Hao-Lin Zhu , Pei-Qin Liao , Xiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046
17. [17]
  Dong Xiang , Kunzhen Li , Kanghua Miao , Ran Long , Yujie Xiong , Xiongwu Kang . Amine-Functionalized Copper Catalysts: Hydrogen Bonding Mediated Electrochemical CO₂ Reduction to C₂ Products and Superior Rechargeable Zn-CO₂ Battery Performance. Acta Physico-Chimica Sinica, 2024, 40(8): 2308027-0. doi: 10.3866/PKU.WHXB202308027
18. [18]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
19. [19]
  Qingying Gao , Tao Luo , Jianyuan Su , Chaofan Yu , Jiazhu Li , Bingfei Yan , Wenzuo Li , Zhen Zhang , Yi Liu . Refinement and Expansion of the Classic Cinnamic Acid Synthesis Experiment. University Chemistry, 2024, 39(5): 243-250. doi: 10.3866/PKU.DXHX202311074
20. [20]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020

Get Citation

PDF

XML

Metrics

PDF Downloads(24)
Abstract views(1652)
HTML views(136)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return