Citation: Sun Haiyu, Wu Guangmiao, Xie Xingang. Synthetic studies towards daphniyunnine B: Construction of AC bicyclic skeleton with two vicinal all carbon quaternary stereocenters[J]. Chinese Chemical Letters, ;2019, 30(8): 1538-1540. doi: 10.1016/j.cclet.2019.06.049 shu

Synthetic studies towards daphniyunnine B: Construction of AC bicyclic skeleton with two vicinal all carbon quaternary stereocenters

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

xiexg@lzu.edu.cn

Received Date: 19 June 2019
Revised Date: 26 June 2019
Accepted Date: 26 June 2019
Available Online: 27 August 2019

Figures(4)

The AC bicyclic skeleton of daphniyunnine B with the required 3 stereocenters (C4, C5 and C8) was accomplished in a concise route which featured two Claisen-type rearrangement reactions to construct the required vicinal all carbon quaternary stereocenters (C5 and C8) and an intramolecular iodocyclization reaction to assemble the cis-confused bicyclic lactam.
- Daphniyunnine B,
- Vicinal quaternary stereocenters,
- Claisen rearrangement,
- Intramolecular iodo-amidation reaction
1. [1]
  (a) J. Kobayashi, T. Kubota, Nat. Prod. Rep. 26 (2009) 936-962;
  (b) H.F. Wu, X.P. Zhang, L.S. Ding, et al., Planta Med. 79 (2013) 1589-1598l;
  (C) A.K. Chattopadhyay, S. Hanessian, Chem. Rev. 117 (2017) 4104-4146.
2. [2]
  B. Kang, P. Jakubec, D. Dixon, J. Nat. Prod. Rep. 31(2014) 550-562. doi: 10.1039/C3NP70115H
3. [3]
  (a) D. Sole, X. Urbaneja, J. Bonjoch, Org. Lett. 7 (2005) 5461-5464;
  (b) F. Diaba, A. Martinez-Laporta, G. Coussanes, I. Fernandez, J. Bonjoch, Tetrahedron 71 (2015) 3642-3651;
  (c) G. Coussanes, J. Bonjoch, Org. Lett. 19 (2017) 878-881;
  (d) F. Sladojevich, I.N. Michaelides, D. Benjamin, J.W. Ward, D.J. Dixon, Org. Lett. 13 (2011) 5132-5135;
  (e) C. Xu, L. Wang, X. Hao, D.Z.G. Wang, J. Org. Chem. 77 (2012) 6307-6313;
  (f) V. Wang, C. Xu, L. Chen, X. Hao, D.Z.G. Wang, Org. Lett. 16 (2014) 1076-1079;
  (g) M. Yang, L. Wang, Z.H. He, et al., Org. Lett. 14 (2012) 5114-5117;
  (h) Y. Yao, G. Liang, Org. Lett. 14 (2012) 5499-5501;
  (i) A.A. Ibrahim, A.N. Golonka, A.M. Lopez, J.L. Stockdill, Org. Lett. 16 (2014) 1072-1075;
  (j) D. Ma, H. Cheng, C. Huang, L. Xu, Tetrahedron Lett. 56 (2015) 2492-2495;
  (k) H. Shao, W. Bao, Z.R. Jing, et al., Org. Lett. 19 (2017) 4648-4651.
4. [4]
  (a) Z.Y. Lu, Y. Li, J. Deng, A. Li, Nat. Chem. 5 (2013) 679-684;
  (b) R. Yamada, Y. Adachi, S. Yokoshima, T. Fukuyama, Angew. Chem. Int. Ed. 55 (2016) 6067-6070;
  (c) J. Li, W.H. Zhang, F. Zhang, Y. Chen, A. Li, J. Am. Chem. Soc. 139 (2017) 14893-14896;
  (d) H. Shi, I.N. Michaelides, B. Darses, et al., J. Am. Chem. Soc. 139 (2017) 17755-17758;
  (e) X.M. Chen, H.J. Zhang, X.K. Yang, et al., Angew. Chem. Int. Ed. 57 (2018) 947-951;
  (f) Y.H. Chen, W.H. Zhang, L. Ren, J. Li, A. Li, Angew. Chem. Int. Ed. 57 (2018) 952-956;
  (g) W.H. Zhang, M. Ding, J. Li, et al., J. Am. Chem. Soc. 140 (2018) 4227-4231;
  (h) B. Xu, B.Y. Wang, W. Xun, F.Y.G. Qiu, Angew. Chem. Int. Ed. 58 (2019) 5754-5757;
  (i) Y.Y. Chen, J.P. Hu, L.D. Guo, et al., Angew. Chem. Int. Ed. 58 (2019) 7390-7394;
  (j) J.X. Zhong, K.W. Chen, Y.Y. Qiu, H.B. He, S.H. Gao, Org. Lett. 21 (2019) 3741-3745.
5. [5]
  (a) Z.M. Wang, Z.M. Xing, L. Liu, et al., ChemistrySelect 1 (2016) 2225-2227;
  (b) H. Zhang, S.Q. Ma, Z.M. Xing, et al., Org. Chem. Front. 4 (2017) 2211-2215;
  (c) L. Liu, H.Y. Song, P. Chen, et al., Org. Chem. Front. 5 (2018) 3013-3017;
  (d) T. Li, G.M. Wu, S.B. Feng, et al., Tetrahedron 75 (2019), doi: http://dx.doi.org/10.1016/j.tet.2019.06.017.
6. [6]
  (a) H. Zhang, S.P. Yang, C.Q. Fan, J. Ding, J.M. Yue, J. Nat. Prod. 69 (2006) 553-557;
  (b) Y.T. Di, H.P. He, Y. Lu, et al., J. Nat. Prod. 69 (2006) 1074-1076.
7. [7]
  K. Spencer, T.L. Anthony, J. Org. Chem. 53(1988) 4006-4014. doi: 10.1021/jo00252a024
1. [1]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
2. [2]
  Chenxi Shang , Boxuan Lu , Chongbei Wu , Shuqing Zhou , Luyan Shi , Tayirjan Taylor Isimjan , Xiulin Yang . Inducing electronic rearrangement through Co₃B-Mo₂B₅ catalysts: Efficient dual-function catalysis for NaBH₄ hydrolysis and 4-nitrophenol reduction. Chinese Chemical Letters, 2025, 36(9): 111152-. doi: 10.1016/j.cclet.2025.111152
3. [3]
  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
4. [4]
  Yi-Kao Xu , Guo-Ping Luo , Liang-Bin Hu , Wei-Min He . Asymmetric Büchner reaction and arene cyclopropanation via copper-catalyzed controllable cyclization of diynes. Chinese Chemical Letters, 2025, 36(8): 111226-. doi: 10.1016/j.cclet.2025.111226
5. [5]
  Zhenguo Zhang , Lanyang Li , Xinlong Zong , Yongheng Lv , Shuanglei Liu , Liang Ji , Xuefei Zhao , Zhenhua Jia , Teck-Peng Loh . "Water" accelerated B(C₆F₅)₃-catalyzed Mukaiyama-aldol reaction: Outer-sphere activation model. Chinese Chemical Letters, 2025, 36(7): 110504-. doi: 10.1016/j.cclet.2024.110504
6. [6]
  Tengfei Xuan , Xinyu Zhang , Wei Han , Yidong Huang , Weiwu Ren . Total synthesis of (+)-taberdicatine B and (+)-tabernabovine B. Chinese Chemical Letters, 2025, 36(2): 109816-. doi: 10.1016/j.cclet.2024.109816
7. [7]
  Tingbo Wang , Yao Luo , Bingyan Hu , Ruiyuan Liu , Jing Miao , Huizhe Lu . Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(11): 278-285. doi: 10.12461/PKU.DXHX202403082
8. [8]
  Ying-Di Hao , Zhi-Qian Lin , Xiao-Yu Guo , Jiao Liang , Can-Kun Luo , Qian-Tao Wang , Li Guo , Yong Wu . Rhodium-catalyzed Doyle-Kirmse rearrangement reactions of sulfoxoniun ylides. Chinese Chemical Letters, 2024, 35(4): 108834-. doi: 10.1016/j.cclet.2023.108834
9. [9]
  Ji-Jia Zhou , Li-Gao Liu , Zhen-Tao Zhang , Hao-Xuan Dong , Xin Lu , Zhou Xu , Xin-Qi Zhu , Bo Zhou , Long-Wu Ye . Copper-catalyzed asymmetric cascade diyne cyclization/Meinwald rearrangement. Chinese Chemical Letters, 2025, 36(9): 110870-. doi: 10.1016/j.cclet.2025.110870
10. [10]
  Zhenhao Wang , Yuliang Tang , Ruyu Li , Shuai Tian , Yu Tang , Dehai Li . Bioinspired synthesis of cochlearol B and ganocin A. Chinese Chemical Letters, 2024, 35(7): 109247-. doi: 10.1016/j.cclet.2023.109247
11. [11]
  Wenling Yuan , Fengli Li , Zhe Chen , Qiaoxin Xu , Zhenhua Guan , Nanyu Yao , Zhengxi Hu , Junjun Liu , Yuan Zhou , Ying Ye , Yonghui Zhang . AbnI: An α-ketoglutarate-dependent dioxygenase involved in brassicicene CH functionalization and ring system rearrangement. Chinese Chemical Letters, 2024, 35(5): 108788-. doi: 10.1016/j.cclet.2023.108788
12. [12]
  Wenyu Gao , Liming Zhang , Chuang Zhao , Lixiang Liu , Xingran Yang , Jinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447
13. [13]
  Ruru Li , Qian Liu , Hui Li , Fengbin Sun , Zhurui Shen . Rational design of dual sites induced local electron rearrangement for enhanced photocatalytic oxygen activation. Chinese Chemical Letters, 2024, 35(11): 109679-. doi: 10.1016/j.cclet.2024.109679
14. [14]
  Huashan Huang , Jingze Chen , Luyun Zhang , Hong Yan , Siqi Li , Fen-Er Chen . Oscillatory flow reactor facilitates fast photochemical Wolff rearrangement toward synthesis of α-substituted amides in flow. Chinese Chemical Letters, 2025, 36(2): 109992-. doi: 10.1016/j.cclet.2024.109992
15. [15]
  Zhen Zhang , Xue-ling Chen , Xiu-Mei Xie , Tian-Yu Gao , Jing Qin , Jun-Jie Li , Chao Feng , Da-Gang Yu . Iron-promoted carbonylation–rearrangement of α-aminoaryl-tethered alkylidenecyclopropanes with CO₂: Facile synthesis of quinolinofurans. Chinese Chemical Letters, 2025, 36(4): 110056-. doi: 10.1016/j.cclet.2024.110056
16. [16]
  Chonglong He , Yulong Wang , Quan-Xin Li , Zichen Yan , Keyuan Zhang , Shao-Fei Ni , Xin-Hua Duan , Le Liu . Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/Smiles rearrangement cascade. Chinese Chemical Letters, 2025, 36(5): 110253-. doi: 10.1016/j.cclet.2024.110253
17. [17]
  Kai Zhou , Ao Sun , Yuchao Wang , Hang Dong , Chenkai Bai , Yidian Mo , Xuyang Ding , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Semisynthesis of rare chondroitin sulfate B and T oligosaccharides. Chinese Chemical Letters, 2025, 36(9): 110783-. doi: 10.1016/j.cclet.2024.110783
18. [18]
  Jinjie Lu , Qikai Liu , Yuting Zhang , Yi Zhou , Yanbo Zhou . Antibacterial performance of cationic quaternary phosphonium-modified chitosan polymer in water. Chinese Chemical Letters, 2024, 35(9): 109406-. doi: 10.1016/j.cclet.2023.109406
19. [19]
  Zhi-Peng Bao , Hefei Yang , Ru-Han A , Yuanrui Wang , Xiao-Feng Wu . Carbonylative five-component synthesis of amides and esters with α-quaternary carbon center. Chinese Chemical Letters, 2025, 36(11): 111150-. doi: 10.1016/j.cclet.2025.111150
20. [20]
  Jun Jiang , Hui Dai , Tao Tu . Two vicinal C(sp³)-F bonds functionalization of perfluoroalkyl halides (PFAHs). Chinese Chemical Letters, 2025, 36(7): 111054-. doi: 10.1016/j.cclet.2025.111054

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(1235)
HTML views(55)

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