A Synthetic Route to Access Allyl-methyl-N-pantothenamide via [2,3]-Wittig Rearrangement
- Corresponding author: Sun Moran, sunmr@zzu.edu.cn
Citation:
Xia Liwen, Zhao Qing, Ba Mengyu, Hu chaoping, Sun Moran, Yang Hua. A Synthetic Route to Access Allyl-methyl-N-pantothenamide via [2,3]-Wittig Rearrangement[J]. Chinese Journal of Organic Chemistry,
;2019, 39(7): 2035-2041.
doi:
10.6023/cjoc201811009
Clifton, G.; Bryant, S. R.; Skinner, C. G. Arch. Biochem. Bioph. 1970, 137, 523.
doi: 10.1016/0003-9861(70)90470-4
(a) Zhang, Y.-M.; Frank, M. W.; Virga, K. G.; Lee, R. E.; Rock, C. O.; Jackowski, S. J. Biolog. Chem. 2004, 279, 50969.
(b) Maršavelski, A. RSC Adv. 2016, 6, 44888.
Hoegl, A.; Darabi, H.; Tran, E.; Awuah, E.; Kerdo, E. S. C.; Habib, E. Biorg. Med. Chem. Lett. 2014, 24, 3274.
doi: 10.1016/j.bmcl.2014.06.013
Akinnusi, T. O.; Vong, K.; Auclair, K. Bioorg. Med. Chem. 2011, 19, 2696.
doi: 10.1016/j.bmc.2011.02.053
Fráter, G. Tetrahedron Lett. 1981, 22, 425
doi: 10.1016/0040-4039(81)80116-5
Tsao, K.-W.; Cheng, C.-Y.; Isobe, M. Org. Lett. 2012, 14, 5274
doi: 10.1021/ol302432d
Hiersemann, M.; Lauterbach, C.; Pollex, A. Eur. J. Org. Chem. 1999, 2713.
Hiersemann, M.; Abraham, L.; Pollex, A. Synlett 2003, 1088.
(a) Yang, H.; Sun, M.; Zhao, S.; Zhu, M.; Xie, Y.; Niu, C. J. Org. Chem. 2013, 78, 339.
(b) Sun, M.; Dai, L; Yang, H.; Liu, H.; Yu, D. Chin. J. Org. Chem. 2018, 38, 2443(in Chinese).
(孙默然, 代磊, 杨华, 刘宏民, 于德泉, 有机化学, 2018, 38, 2443.)
(c) Zhou, H.; Sun, M.; Cao, Q.; Bai, L.; Xie, Y.; Yang, H. Chin. J. Org. Chem. 2013, 33, 2515(in Chinese).
(周航, 孙默然, 曹其伟, 朱明, 白磊阳, 谢阳娜, 杨华, 有机化学, 2013, 33, 2515.)
Marshall, J. A.; Lebreton, J. J. Am. Chem. Soc. 1988, 110, 2925.
doi: 10.1021/ja00217a039
(a) Hirokawa, Y.; Kitamura, M.; Maezaki, N. Tetrahedron: Asymmetry 2008, 19, 1167.
(b) Barrett, I. M.; Breeden, S. W. Tetrahedron: Asymmetry 2004, 15, 3015.
Seco, J. M.; Quiñoá, E.; Riguera, R. Tetrahedron:Asymmetry 2001, 12, 2915.
doi: 10.1016/S0957-4166(01)00508-0
(a) Osamu, T.; Koichi, M.; Takeshi, N. Chem. Lett. 1987, 16, 69.
(b) Fujimoto, K, Nakai, T. Tetrahedron Lett. 1994, 35, 5019.
Diéguez, H. R.; López, A.; Domingo, V.; Arteaga, J. F.; Dobado, J. A.; Herrador, M. M. J. Am. Chem. Soc. 2010, 132, 254.
doi: 10.1021/ja906083c
Hughes, G.; Lautens, M.; Wen, C. Org. Lett. 2000, 2, 107.
doi: 10.1021/ol991170n
Vong, K. K. H.; Maeda, S.; Tanaka, K. Chem.-Eur. J. 2016, 22, 18865.
doi: 10.1002/chem.201604247
Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351
Zixu Xie , Pengfei Zhang , Ziyao Zhang , Chen Chen , Xing Wang . The choice of antimicrobial polymers: Hydrophilic or hydrophobic?. Chinese Chemical Letters, 2024, 35(9): 109768-. doi: 10.1016/j.cclet.2024.109768
Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
Zhao Gu , Yunhui Yang , Song Ye , Congyang Wang . 2,3-Arylacylation of allenes through synergetic catalysis of palladium and N-heterocyclic carbene. Chinese Chemical Letters, 2025, 36(5): 110334-. doi: 10.1016/j.cclet.2024.110334
Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
Yaxian Liang , Qingyi Li , Liwei Hu , Ruohan Zhai , Fan Liu , Lin Tan , Xiaofei Wang , Huixu Xie . Environmentally friendly polylysine gauze dressing for an innovative antimicrobial approach to infected wound management. Chinese Chemical Letters, 2024, 35(10): 109459-. doi: 10.1016/j.cclet.2023.109459
Hao Sun , Shengke Li , Qian Liu , Minzan Zuo , Xueqi Tian , Kaiya Wang , Xiao-Yu Hu . Supramolecular prodrug vesicles for selective antimicrobial therapy employing a chemo-photodynamic strategy. Chinese Chemical Letters, 2025, 36(3): 109999-. doi: 10.1016/j.cclet.2024.109999
Yunfen Gao , Liying Wang , Chufan Zhou , Yi Zhao , Hai Huang , Jun Wu . Low-dimensional antimicrobial nanomaterials in anti-infection treatment and wound healing. Chinese Chemical Letters, 2025, 36(3): 110028-. doi: 10.1016/j.cclet.2024.110028
Chenhao Zhang , Qian Zhang , Yezhou Hu , Hanyu Hu , Junhao Yang , Chang Yang , Ye Zhu , Zhengkai Tu , Deli Wang . N-doped carbon confined ternary Pt2NiCo intermetallics for efficient oxygen reduction reaction. Chinese Chemical Letters, 2025, 36(3): 110429-. doi: 10.1016/j.cclet.2024.110429
Xuehua SUN , Min MA , Jianting LIU , Rui TIAN , Hongmei CHAI , Huali CUI , Loujun GAO . Pr/N co-doped biomass carbon dots with enhanced fluorescence for efficient detection of 2,4-dinitrophenylhydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 561-573. doi: 10.11862/CJIC.20240294
Chengyao Zhao , Jingyuan Liao , Yuxiang Zhu , Yiying Zhang , Lianjie Zhai , Junrong Huang , Hengzhi You . Polystyrene-supported phosphoric-acid catalyzed atroposelective construction of axially chiral N-aryl benzimidazoles. Chinese Chemical Letters, 2025, 36(6): 110337-. doi: 10.1016/j.cclet.2024.110337
Mao-Fan Li , Ming‐Yu Guo , De-Xuan Liu , Xiao-Xian Chen , Wei-Jian Xu , Wei-Xiong Zhang . Multi-stimuli responsive behaviors in a new chiral hybrid nitroprusside salt (R-3-hydroxypyrrolidinium)2[Fe(CN)5(NO)]. Chinese Chemical Letters, 2024, 35(12): 109507-. doi: 10.1016/j.cclet.2024.109507
Le Ye , Wei-Xiong Zhang . Structural phase transition in a new organic-inorganic hybrid post-perovskite: (N,N-dimethylpyrrolidinium)[Mn(N(CN)2)3]. Chinese Journal of Structural Chemistry, 2024, 43(6): 100257-100257. doi: 10.1016/j.cjsc.2024.100257
Shijie Li , Ke Rong , Xiaoqin Wang , Chuqi Shen , Fang Yang , Qinghong Zhang . Design of Carbon Quantum Dots/CdS/Ta3N5 S-Scheme Heterojunction Nanofibers for Efficient Photocatalytic Antibiotic Removal. Acta Physico-Chimica Sinica, 2024, 40(12): 2403005-. doi: 10.3866/PKU.WHXB202403005
Ruiying Liu , Li Zhao , Baishan Liu , Jiayuan Yu , Yujie Wang , Wanqiang Yu , Di Xin , Chaoqiong Fang , Xuchuan Jiang , Riming Hu , Hong Liu , Weijia Zhou . Modulating pollutant adsorption and peroxymonosulfate activation sites on Co3O4@N,O doped-carbon shell for boosting catalytic degradation activity. Chinese Journal of Structural Chemistry, 2024, 43(8): 100332-100332. doi: 10.1016/j.cjsc.2024.100332
Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp3)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO2 Reduction by Modified g-C3N4. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-. doi: 10.3866/PKU.WHXB202408005
Liang Ma , Zhou Li , Zhiqiang Jiang , Xiaofeng Wu , Shixin Chang , Sónia A. C. Carabineiro , Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2024.100416
Long TANG , Yaxin BIAN , Luyuan CHEN , Xiangyang HOU , Xiao WANG , Jijiang WANG . Syntheses, structures, and properties of three coordination polymers based on 5-ethylpyridine-2,3-dicarboxylic acid and N-containing ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1975-1985. doi: 10.11862/CJIC.20240180
Xiuzheng Deng , Changhai Liu , Xiaotong Yan , Jingshan Fan , Qian Liang , Zhongyu Li . Carbon dots anchored NiAl-LDH@In2O3 hierarchical nanotubes for promoting selective CO2 photoreduction into CH4. Chinese Chemical Letters, 2024, 35(6): 108942-. doi: 10.1016/j.cclet.2023.108942