Citation: Song Huayue, Liu Lin, Xie Xingang. Asymmetric Total Synthesis of the Possible Structure 1b of 15-Oxopuupehenoic Acid[J]. Chinese Journal of Organic Chemistry, ;2020, 40(10): 3420-3425. doi: 10.6023/cjoc202005058 shu

Asymmetric Total Synthesis of the Possible Structure 1b of 15-Oxopuupehenoic Acid

Song Huayue ^† ,
Liu Lin ^† ,
Xie Xingang ^,

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000

Corresponding author: Xie Xingang, xiexg@lzu.edu.cn
Received Date: 22 May 2020
Revised Date: 29 May 2020
Available Online: 8 June 2020
Fund Project: the National Natural Science Foundation of China 21472079Project supported by the National Natural Science Foundation of China (No. 21472079)

Figures(4)

15-Oxopuupehenoic acid is a new merosesquiterpenoid isolated in 2009 by Crews group from the crude sponge extracts prioritized a Papua New Guinea collection of Hyrtios sp. Its possible structure was deduced to be tetracyclic chromanones 1a~1b or benzo[c]oxepin-1(3H)-ones 1c~1d based on the spectra data, and later determinded to be 1a by analysis of its gHMBC correlations spectra. Recently Alvarez-Manzaneda and Chahboun group obtained 1a by chemical synthesis which spectra data did not match well with those of natural 15-oxopuupehenoic acid. We started from R-(—)-carvone and approched its possible structure 1b through a convergent coupling-cyclization strategy. Our sythesis featured Suzuki carbonylative coupling reaction and KOH promoted intramolecular cyclization reaction to construct the unique chromanone subunit. The spectra data of synthetic 1b did not match well with those of natural 15-oxopuupehenoic acid either which indicated its structure needed revision.
- 15-oxopuupehenoic acid,
- Suzuki carbonylative coupling,
- KOH promotion,
- intramolecular cyclization,
- chromanone
1. [1]
  (a) Kohmoto, S.; McConnell, O. J.; Wright, A.; Koehn, F.; Thompson, W.; Lui, M.; Snader, K. M. J. Nat. Prod. 1987, 50, 336.
  (b) Sova, V.; Fedoreev, S. A. Khim. Prir. Soedin. 1990, 497.
  (c) Longley, R. E.; McConnel, O. J.; Essich, E.; Harmody, D. J. Nat. Prod. 1993, 56, 915.
  (d) El Sayed, K. A.; Dunbar, D. C.; Perry, T. L.; Wilkins, S. P.; Hamann, M. T.; Greenplate, J. T.; Wideman, M. A. J. Agric. Food Chem. 1997, 45, 2735.
  (e) Faulkner, D. J. Nat. Prod. Rep. 1998, 15, 113 and references cited therein.
  (f) ourguet-Kondracki, M. L.; Lacombe, F.; Guyot, M. J. Nat. Prod. 1999, 62, 1304.
  (g) Popov, A. M.; Stekhova, S. I.; Utkina, N. K.; Rebachuk, N. M. Pharm. Chem. J. 1999, 33, 71.
  (h) El Sayed, K. A.; Bartyzel, P.; Shen, X.; Perry, T. L.; Zjawiony, J. K.; Hamann, M. T. Tetrahedron 2000, 56, 949.
  (i) Takamatsu, S.; Hodges, T. W.; Rajbhandari, I.; Gerwick, H.; Hamann, M. T.; Nagle, D. G. J. Nat. Prod. 2003, 66, 605.
  (j) Pina, I. C.; Sanders, M. L.; Crews, P. J. J. Nat. Prod. 2003, 66, 2.
  (k) Hamann, M. T. Curr. Pharm. Des. 2003, 9, 879.
  (l) Graus, G. A.; Nguyen, T.; Bae, J.; Hostetter, J.; Steadham, E. Tetrahedron 2004, 60, 4223.
2. [2]
  Robinson, S. J.; Hoobler, E. K.; Riener, M.; Loveridge, S. T.; Tenney, K.; Valeriote, F. A.; Holman, T. R.; Crews, P. J. Nat. Prod. 2009, 72, 1857. doi: 10.1021/np900465e
3. [3]
  Boulifa, E.; Fernández, A.; Alvarez, E.; Alvarez-Manzaneda, R.; Mansour, A. I.; Chahboun, R.; Alvarez-Manzaneda, E. J. Org. Chem. 2014, 79, 10689. doi: 10.1021/jo502048y
4. [4]
  Liu, L.; Song, H.-Y.; Chen, P.; Yuan, Z.-Y.; Feng, S.-B.; Zhang, W.-W.; Fang, B.-W.; Xie, X.-G.; She, X.-G. Org. Chem. Front. 2018, 5, 3013. doi: 10.1039/C8QO00901E
5. [5]
  Sumino, S.; Ui, T.; Ryu, I. Org. Chem. Front. 2015, 2, 1085. doi: 10.1039/C5QO00185D
6. [6]
  Wang, Z.-J.; Wang, X.-Y.; Wang, X.; Liang, Z.-W.; Xu, X. Catal. Commun. 2017, 101, 10. doi: 10.1016/j.catcom.2017.06.005
7. [7]
  Wójcik, P.; Sygellou, L.; Gniewek, A.; Skarżyńska, A.; Trzeciak, A. Chem. Cat. Chem. 2017, 9, 4397.
8. [8]
  Gautam, P.; Bhanage, B. M. J. Org. Chem. 2015, 80, 7810. doi: 10.1021/acs.joc.5b01160
9. [9]
  Ketike, T.; Velpula, V. R. K.; Madduluri, V. R.; Kamaraju, S. R. R.; Burri, D. R. ChemistrySelect 2018, 3, 7164. doi: 10.1002/slct.201801100
10. [10]
  Song, H.-Y.; Liu, L.; Yang, M.-Y.; Wu, G.-M.; Chen, P.; Xie, X.-G.; She, X.-G. Org. Chem. Front. 2020, 7, 35. doi: 10.1039/C9QO01027K
11. [11]
  Gesson, J. P.; Jacquesy, J. C.; Renoux, B. Tetrahedron 1989, 45, 5853. doi: 10.1016/S0040-4020(01)89112-2
1. [1]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
2. [2]
  Zhongyan Cao , Youzhi Xu , Menghua Li , Xiao Xiao , Xianqiang Kong , Deyun Qian . Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes. University Chemistry, 2025, 40(4): 277-281. doi: 10.12461/PKU.DXHX202407017
3. [3]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
4. [4]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
5. [5]
  Yuan Yang , Jian Zhang , Shaomin Shuang . Promoting an All-English Teaching Approach in the Chemistry English Curriculum to Enhance Internationalization. University Chemistry, 2025, 40(5): 238-243. doi: 10.12461/PKU.DXHX202403079
6. [6]
  .
  CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
  . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.
7. [7]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
8. [8]
  Wenyan Dan , Weijie Li , Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060
9. [9]
  Jiaxun Wu , Mingde Li , Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098
10. [10]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
11. [11]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
12. [12]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
13. [13]
  Yufang GAO , Nan HOU , Yaning LIANG , Ning LI , Yanting ZHANG , Zelong LI , Xiaofeng LI . Nano-thin layer MCM-22 zeolite: Synthesis and catalytic properties of trimethylbenzene isomerization reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1079-1087. doi: 10.11862/CJIC.20240036
14. [14]
  Lijun Huo , Mingcun Wang , Tianyi Zhao , Mingjie Liu . Exploration of Undergraduate and Graduate Integrated Teaching in Polymer Chemistry with Aerospace Characteristics. University Chemistry, 2024, 39(6): 103-111. doi: 10.3866/PKU.DXHX202312059
15. [15]
  Peipei Sun , Jinyuan Zhang , Yanhua Song , Zhao Mo , Zhigang Chen , Hui Xu . 引入内建电场增强光载流子分离以促进H₂的生产. Acta Physico-Chimica Sinica, 2024, 40(11): 2311001-. doi: 10.3866/PKU.WHXB202311001
16. [16]
  Jianyin He , Liuyun Chen , Xinling Xie , Zuzeng Qin , Hongbing Ji , Tongming Su . ZnCoP/CdLa₂S₄肖特基异质结的构建促进光催化产氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2404030-. doi: 10.3866/PKU.WHXB202404030
17. [17]
  Shipeng WANG , Shangyu XIE , Luxian LIANG , Xuehong WANG , Jie WEI , Deqiang WANG . Piezoelectric effect of Mn, Bi co-doped sodium niobate for promoting cell proliferation and bacteriostasis. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1919-1931. doi: 10.11862/CJIC.20240094
18. [18]
  Dongcheng Liu , Xiaokun Li , Huancheng Hu , Cunji Gao , Qiong Hu , Shuting Li , Yuning Liang . Chemistry Experimental Teaching Reform for the Promotion of Training Exceptional Chemistry Teachers for Normal Schools. University Chemistry, 2024, 39(8): 1-6. doi: 10.3866/PKU.DXHX202311072
19. [19]
  Wei Yan , Cailing Wang , Li Wang , Yonghai Song . Promoting the Reform of Basic Chemistry Experimental Courses through Laboratory Skill Competition. University Chemistry, 2024, 39(10): 189-194. doi: 10.3866/PKU.DXHX202403042
20. [20]
  Yan Liu , Xiaojun Han , Ping Xu , Guoxu Zhang , Yu Wang , Zhicheng Zhang , Dianpeng Qi . “Five Measures” Based Science and Education Integration Experimental Teaching Mode to Promote the Construction of “Specialized Experiment” Curriculum. University Chemistry, 2024, 39(10): 299-307. doi: 10.12461/PKU.DXHX202405002

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(1081)
HTML views(123)

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