Home

Citation: Sun Moran, Dai Lei, Yang Hua, Liu Hongmin, Yu Dequan. Enantioselective Synthesis of Core Structures of Hydramicromelins A, B and C[J]. Chinese Journal of Organic Chemistry, ;2018, 38(9): 2443-2449. doi: 10.6023/cjoc201802017 shu

Enantioselective Synthesis of Core Structures of Hydramicromelins A, B and C

Sun Moran ^a,b ,
Dai Lei ^a,b ,
Yang Hua ^a,b,, ,
Liu Hongmin ^a,b,, ,
Yu Dequan ^a

a.
School of Pharmaceutical Science, Zhengzhou University, Zhengzhou 450001
b.
Collaborative Innovation Center of New Drug Research and Safety Evaluation, Zhengzhou 450001

Corresponding author: Yang Hua, yanghua@zzu.edu.c Liu Hongmin, liuhm@zzu.edu.cn
Received Date: 9 February 2018
Revised Date: 28 March 2018
Available Online: 27 September 2018
Fund Project: the National Natural Science Foundation of China 21302175the National Natural Science Foundation of China 21372205Project supported by the National Natural Science Foundation of China (Nos. 21372205, 21302175) and the Basic Research Project of Science and Technology Department of Henan Province (No. 132300410028)the Basic Research Project of Science and Technology Department of Henan Province 132300410028

Figures(5)

Hydramicromelins A~C are coumarin compounds with unique chemical structure and biological activity. With[2,3]-Meisenheimer rearrangemen as a key reaction which has been developed in our laboratory, the core structures of Hydramicromelin A, B and C were synthesized from L-phenylglycine. The route included Wittig reaction, [2,3]-Meisenheimer rearrangement, epoxidation and dihydroxylation reaction, and it was high-yield and high-enantioselectivity.
- hydramicromelins A, B and C,
- [2, 3]-Meisenheimer rearrangement,
- chiral tertiary alcohol,
- epoxidation
1. [1]
  Lambert, J. A.; Price, J. R.; Redcliffe, A. H. Aust. J. Chem. 1967, 20, 973.
2. [2]
  Cassady, J. M.; Ojima, N.; Chang, C. J.; Mclaughlin, J. L. J. Nat. Prod. 1979, 42, 274. doi: 10.1021/np50003a005
3. [3]
  He, H. P.; Zou, Y.; Shen, Y. M.; Hao, X. J. Chin. Chem. Lett. 2001, 12, 603.
4. [4]
  Huo, X.; Ren, X.; Xu, Y.; Li, X.; She, X.; Pan, X. Tetrahedron:Asymmetry 2008, 19, 343. doi: 10.1016/j.tetasy.2008.01.006
5. [5]
  Yang, H.; Sun, M.; Zhao, S.; Zhu, M.; Xie, Y.; Niu, C.; Li, C. J. Org. Chem. 2013, 78, 339. doi: 10.1021/jo302203g
6. [6]
  (a) Xie, Y.; Sun, M.; Zhou, H.; Cao, Q.; Gao, K.; Niu, C.; Yang, H. J. Org. Chem. 2013, 78, 10251.
  (b) Sun, M.; Xie, Y.; Gu, J.; Yang, H. Can. J. Chem. 2013, 91, 738.
  (c) Gao, K.; Sun, M.; Zhu, M.; Zhou, H.; Cao, Q.; Yang, H. Chin. J. Org. Chem. 2013, 33, 1939.
  (d) Sun, M.; Gao, K.; Zheng, J.; Lai, Y.; Yang, H. Res. Chem. Intermed. 2015, 41, 1181.
  (d) Sun, M.; Li, Y.; Shi, X.; Niu, C.; Yang, H. ARKIVOC 2016, 4, 172.
7. [7]
  (a) Mosa, F.; Thirsk, C.; Vaultier, M.; Maw, G.; Whiting, A. Org. Synth. 2008, 85, 219.
  (b) Denis, J. N.; Correa, A.; Greene, A. E. J. Org. Chem. 1991, 56, 6939.
8. [8]
  (a) Fujii, T.; Itaya, T.; Matsubara, S. Chem. Pharm. Bull. 1989, 37, 1758.
  (b) Pihko, P. M.; Koskinen, A. M. J. Org. Chem. 1998, 63, 92.
9. [9]
  Hoffmann, R. W. Chem. Rev. 1989, 89, 1841. doi: 10.1021/cr00098a009
10. [10]
  (a) Jiang, B.; Chen, Z.; Tang, X. Org. Lett. 2002, 4, 3451.
  (b) Infante, R.; Nieto, J.; Andrés, C. Chem.-Eur. J. 2012, 18, 4375.
  (c) Blay, G.; Fernández, I.; Marco-Aleixandre, A.; Pedro, J. R. Org. Lett. 2006, 8, 1287.
11. [11]
12. [12]
  Wu, H.; Yang, B.; Zhu, L.; Lu, R.; Li, G.; Lu, H. Org. Lett. 2016, 18, 5804. doi: 10.1021/acs.orglett.6b02706
1. [1]
  Zhenxing Liu , Jiaen Hu , Zishi Cheng , Xinqi Hao . 基础有机化学教学中烯烃的氧化反应. University Chemistry, 2025, 40(6): 139-144. doi: 10.12461/PKU.DXHX202408107
2. [2]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015
3. [3]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
4. [4]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
5. [5]
  Jiying Liu , Zehua Li , Wenjing Zhang , Donghui Wei . Molecular Orbital and Nucleus-Independent Chemical Shift Calculations for C₆H₆ and B₁₂H₁₂^2-: A Computational Chemistry Experiment. University Chemistry, 2025, 40(3): 186-192. doi: 10.12461/PKU.DXHX202406085
6. [6]
  Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . 两步焙烧法制备大比表面积和结晶性增强超薄g-C₃N₄纳米片及其高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-. doi: 10.3866/PKU.WHXB202406019
7. [7]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
8. [8]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
9. [9]
  Tao Wen , Tao Zhang , Changguo Sun , Jinyu Liu . Preparation of Dess-Martin Reagent and Its Application in Oxidizing Cyclohexanol. University Chemistry, 2024, 39(5): 20-26. doi: 10.3866/PKU.DXHX202309055
10. [10]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
11. [11]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
12. [12]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
13. [13]
  Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174
14. [14]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
15. [15]
  Entian Cui , Yulian Lu , Zhaoxia Li , Zhilei Chen , Chengyan Ge , Jizhou Jiang . Interfacial B-O bonding modulated S-scheme B-doped N-deficient C₃N₄/O-doped-C₃N₅ for efficient photocatalytic overall water splitting. Chinese Chemical Letters, 2025, 36(1): 110288-. doi: 10.1016/j.cclet.2024.110288
16. [16]
  Tong Zhou , Xue Liu , Liang Zhao , Mingtao Qiao , Wanying Lei . Efficient Photocatalytic H₂O₂ Production and Cr(VI) Reduction over a Hierarchical Ti₃C₂/In₄SnS₈ Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020
17. [17]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
18. [18]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
19. [19]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
20. [20]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(915)
HTML views(149)

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