Citation: Jiao Xu, Bo Liu. Total synthesis of norleucosceptroids F and G[J]. Chinese Chemical Letters, ;2015, 26(11): 1341-1344. doi: 10.1016/j.cclet.2015.07.004 shu

Total synthesis of norleucosceptroids F and G

Jiao Xu ^a ,
Bo Liu ^a,b,,

1.
a Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China;
2.
b State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, China

Corresponding author: Bo Liu,
Received Date: 6 May 2015
Available Online: 11 June 2015

First total synthesis of norleucosceptroids F and G has been achieved through key steps of Michael-Aldol cascade, oxa-Michael cyclization-dehydration-deprotection cascade and cross metathesis (CM), this work developed a general and concise method to the synthesis of leucosceptroid and norleucosceptroid.
- Total synthesis
1. [1]
  [1] (a) S.H. Luo, Q. Luo, X.M. Niu, et al., Glandular trichomes of Leucosceptrum canum harbor defensive sesterterpenoids, Angew. Chem. Int. Ed. 49 (2010) 4471-4475; (b) S.H. Luo, L.H. Weng, M.J. Xie, et al., Defensive sesterterpenoids with unusual antipodal cyclopentenones from the leaves of Leucosceptrum canum, Org. Lett. 13 (2011) 1864-1867; (c) S.H. Luo, J. Hua, C.H. Li, et al., New antifeedant C20 terpenoids from Leucosceptrum canum, Org. Lett. 14 (2012) 5768-5771; (d) S.H. Luo, J. Hua, X.M. Niu, et al., Defense sesterterpenoid lactones from Leucosceptrum canum, Phytochemistry 86 (2013) 29-35; (e) S.H. Luo, J. Hua, C.H. Li, et al., Unusual antifeedant spiro-sesterterpenoid from the flowers of Leucosceptrum canum, Tetrahedron Lett. 54 (2013) 235-237; (f) S.H. Luo, C.L. Hugelshofer, J. Hua, et al., Unraveling the metabolic pathway in Leucosceptrum canum by isolation of new defensive leucosceptroid degradation products and biomimetic model synthesis, Org. Lett. 16 (2014) 6416-6419.
2. [2]
  [2] C.H. Li, S.X. Jing, S.H. Luo, et al., Peltate glandular trichomes of Colquhounia coccinea var. mollis harbor a new class of defensive sesterterpenoids, Org. Lett. 15 (2013) 1694-1697.
3. [3]
  [3] G.Z. Yue, X. Huang, B. Liu, Progress in the total syntheses oftrans-hydrindanecontaining terpenoids, Chin. J. Org. Chem. 33 (2013) 1167.
4. [4]
  [4] (a) J. Xie, Y. Ma, D.A. Horne, Asymmetric synthesis of the core structure of leucosceptroids A-D, J. Org. Chem. 76 (2011) 6169-6176; (b) X. Huang, L.Q. Song, J. Xu, et al., Asymmetric total synthesis of leucosceptroid B, Angew. Chem. Int. Ed. 52 (2013) 952-955; (c) C.L. Hugelshofer, T. Magauer, A general entry to antifeedant sesterterpenoids: total synthesis of (+)-norleucosceptroid A, (-)-norleucosceptroid B, and (-)- leucosceptroid K, Angew. Chem. Int. Ed. 53 (2014) 11351-11355; (d) C.L. Hugelshofer, T. Magauer, Total synthesis of the leucosceptroid family of natural products, J. Am. Chem. Soc. 137 (2015) 3807-3810; (e) C.L. Hugelshofer, T. Magauer, Strategies for the synthesis of antifeedant leucosceptroid natural products, Synlett 26 (2015) 572-579; (f) S. Guo, J. Liu, D.W. Ma, Total synthesis of leucosceptroids A and B, Angew. Chem. Int. Ed. 54 (2015) 1298-1301.
5. [5]
  [5] A.K. Chatterjee, T.L. Choi, D.P. Sanders, et al., A general model for selectivity in olefin cross metathesis, J. Am. Chem. Soc. 125 (2003) 11360-11370.
1. [1]
  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
2. [2]
  Jingping Hu , Jing Xu . Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C₁₄–epi-deoxycalyciphylline H. Chinese Chemical Letters, 2024, 35(4): 108733-. doi: 10.1016/j.cclet.2023.108733
3. [3]
  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
4. [4]
  Peng Chen , Lijuan Liang , Yufei Zhu , Zhimin Xing , Zhenhua Jia , Teck-Peng Loh . Strategies for constructing seven-membered rings: Applications in natural product synthesis. Chinese Chemical Letters, 2024, 35(6): 109229-. doi: 10.1016/j.cclet.2023.109229
5. [5]
  Huimin Luan , Qinming Wu , Jianping Wu , Xiangju Meng , Feng-Shou Xiao . Templates for the synthesis of zeolites. Chinese Journal of Structural Chemistry, 2024, 43(4): 100252-100252. doi: 10.1016/j.cjsc.2024.100252
6. [6]
  Zhaojun Liu , Zerui Mu , Chuanbo Gao . Alloy nanocrystals: Synthesis paradigms and implications. Chinese Journal of Structural Chemistry, 2023, 42(11): 100156-100156. doi: 10.1016/j.cjsc.2023.100156
7. [7]
  Hui Jin , Qin Cai , Peiwen Liu , Yan Chen , Derong Wang , Weiping Zhu , Yufang Xu , Xuhong Qian . Multistep continuous flow synthesis of Erlotinib. Chinese Chemical Letters, 2024, 35(4): 108721-. doi: 10.1016/j.cclet.2023.108721
8. [8]
  Caihong Mao , Yanfeng He , Xiaohan Wang , Yan Cai , Xiaobo Hu . Synthesis and molecular recognition characteristics of a tetrapodal benzene cage. Chinese Chemical Letters, 2024, 35(8): 109362-. doi: 10.1016/j.cclet.2023.109362
9. [9]
  Mei Peng , Wei-Min He . Photochemical synthesis and group transfer reactions of azoxy compounds. Chinese Chemical Letters, 2024, 35(8): 109899-. doi: 10.1016/j.cclet.2024.109899
10. [10]
  Liyong Ding , Zhenhua Pan , Qian Wang . 2D photocatalysts for hydrogen peroxide synthesis. Chinese Chemical Letters, 2024, 35(12): 110125-. doi: 10.1016/j.cclet.2024.110125
11. [11]
  Xiaoyu Chen , Jiahao Hu , Jingyi Lin , Haiyang Huang , Changqing Ye , Hongli Bao . Biisoindolylidene solvatochromic fluorophores: Synthesis and photophysical properties. Chinese Chemical Letters, 2025, 36(2): 109923-. doi: 10.1016/j.cclet.2024.109923
12. [12]
  Yuqing Liu , Yu Yang , Yuhan E , Changlong Pang , Di Cui , Ang Li . Insight into microbial synthesis of metal nanomaterials and their environmental applications: Exploration for enhanced controllable synthesis. Chinese Chemical Letters, 2024, 35(11): 109651-. doi: 10.1016/j.cclet.2024.109651
13. [13]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
14. [14]
  Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147
15. [15]
  Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
16. [16]
  Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
17. [17]
  Hao Deng , Yuxin Hui , Chao Zhang , Qi Zhou , Qiang Li , Hao Du , Derek Hao , Guoxiang Yang , Qi Wang . MXene−derived quantum dots based photocatalysts: Synthesis, application, prospects, and challenges. Chinese Chemical Letters, 2024, 35(6): 109078-. doi: 10.1016/j.cclet.2023.109078
18. [18]
  Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
19. [19]
  Xu-Hui Yue , Xiang-Wen Zhang , Hui-Min He , Lei Qiao , Zhong-Ming Sun . Synthesis, chemical bonding and reactivity of new medium-sized polyarsenides. Chinese Chemical Letters, 2024, 35(7): 108907-. doi: 10.1016/j.cclet.2023.108907
20. [20]
  Yuanjin Chen , Xianghui Shi , Dajiang Huang , Junnian Wei , Zhenfeng Xi . Synthesis and reactivity of cobalt dinitrogen complex supported by nonsymmetrical pincer ligand. Chinese Chemical Letters, 2024, 35(7): 109292-. doi: 10.1016/j.cclet.2023.109292

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(669)
HTML views(12)

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