Citation: Mei Xu, Tian-Yun Fan, Jian-Xin Zhang, Xiao-Jiang Hao, Sheng Liu. A novel synthesis route to furo[3,2-a]carbazole[J]. Chinese Chemical Letters, ;2015, 26(3): 282-284. doi: 10.1016/j.cclet.2014.11.026 shu

A novel synthesis route to furo[3,2-a]carbazole

1.
a The Key Laboratory of Chemistry for Natural Products of Guizhou Province, Chinese Academy of Sciences, Guiyang 550002, China;
2.
b Guizhou University, Guiyang 550002, China

Corresponding author: Sheng Liu,
Received Date: 24 June 2014
Available Online: 23 October 2014
Fund Project: The work was financially supported by NSFC (No. 21102026) (No. 21102026)

In this paper, we report a novel approach to the heteroaryl-condensed nuclei of natural furo[3,2-a]carbazole alkaloids. Our synthetic studies use N-phthaloyl tryptophan methyl ester as starting material and zinc ion mediated transamination reaction as the key step. This work also implicated a novel strategy to assemble other [a]-fused carbazoles.
- Synthesis,
- Furo[3,2-a]carbazole,
- Transamination
1. [1]
  [1] A.W. Schmidt, K.R. Reddy, H.J. Knölker, Occurrence, biogenesis, and synthesis of biologically active carbazole alkaloids, Chem. Rev. 112 (2012) 3193-3328.
2. [2]
  [2] C. Ito, H. Furukawa, New carbazole alkaloids from Murraya euchrestifolia Hayata, Chem. Pharm. Bull. 38 (1990) 1548-1550.
3. [3]
  [3] T.S. Wu, S.C. Huang, P.L. Wu, Pyrano-and furocarbazole alkaloids from the root bark of Clausena excavate, Heterocycles 45 (1997) 969-973.
4. [4]
  [4] For review see: W. Fröhner, M.P. Krahl, K.R. Reddy, et al., Transition metal complexes in organic synthesis, part 73, Synthetic routes to naturally occurring furocarbazoles, Heterocycles 63 (2004) 2393-2407.
5. [5]
  [5] Y. Xia, Z.X. Liu, Q. Xiao, et al., Rhodium(II)-catalyzed cyclization of bis(N-tosylhydrazone) s: an efficient approach towards polycyclic aromatic compounds, Angew. Chem. Int. Ed. 51 (2012) 5714-5717.
6. [6]
  [6] S.C. Pelly, C.J. Parkinson, W.A.L. van Otterlo, et al., Metathesis reactions for the synthesis of ring-fused carbazoles, J. Org. Chem. 70 (2005) 10474-10481.
7. [7]
  [7] S. Ohta, M. Okamoto, Synthesis of carbonyl compouds via biogenetic-type transamination reaction, Synthesis 9 (1982) 756-758.
8. [8]
  [8] A. Papanikos, J. Rademann, M. Meldal, a-Ketocarbonyl peptides: a general approach to reactive resin-bound intermediates in the synthesis of peptide isosteres for protease inhibitor screening on solid support, J. Am. Chem. Soc. 123 (2001) 2176-2181.
9. [9]
  [9] E.J. Corey, D.Y. Gin, R.S. Kania, Enantioselective total synthesis of ecteinascidin 743, J. Am. Chem. Soc. 118 (1996) 9202-9203.
10. [10]
  [10] S. Liu, Y.M. Cui, F.J. Nan, Total synthesis of the originally proposed and revised structures of scleritodermin A, Org. Lett. 10 (2008) 3765-3768.
11. [11]
  [11] C.J. Pearce, T.W. Doyle, S. Forenza, et al., The biosynthetic origins of rebeccamycin, J. Nat. Prod. 51 (1988) 937-940.
12. [12]
  [12] T. Nishizawa, S. Grüschow, D.H.E. Jayamaha, et al., Enzymatic assembly of the bis-Indole core of rebeccamycin, J. Am. Chem. Soc. 128 (2006) 724-725.
13. [13]
  [13] D.M. Tapiolas, B.F. Bowden, E. Abou-Mansour, et al., Eusynstyelamides A, B, and C, nNOS inhibitors, from the ascidian Eusynstyela latericius, J. Nat. Prod. 72 (2009) 1115-1120.
14. [14]
  [14] P. Grieco, Y.S. Hon, A. Perez-Medrano, Convergent, enantiospecific total synthesis of the novel cyclodepsipeptide (+)-jasplakinolide (jaspamide), J. Am. Chem. Soc. 110 (1988) 1630-1631.
15. [15]
  [15] N. Wahlström, I. Romero, J. Bergman, Synthesis of metabolites of the Ah receptor ligand 6-formylindolo[3, 2-b]carbazole, Eur. J. Org. Chem. 12 (2004) 2593-2602.
1. [1]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
2. [2]
  Huiju Cao , Lei Shi . sp¹-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
3. [3]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
4. [4]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
5. [5]
  Ying Chen , Ronghua Yan , Weiyan Yin . Research Progress on the Synthesis of Metal Single-Atom Catalysts and Their Applications in Electrocatalytic Hydrogen Evolution Reactions. University Chemistry, 2025, 40(9): 344-353. doi: 10.12461/PKU.DXHX202503066
6. [6]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
7. [7]
  Yuanyu YANG , Jianhua XUE , Yujia BAI , Lulu CUI , Dongdong YANG , Qi MA . Design, synthesis, and detection of Al³⁺ of two zinc complexes based on Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1207-1216. doi: 10.11862/CJIC.20250005
8. [8]
  Ruofan Yin , Zhaoxin Guo , Rui Liu , Xian-Sen Tao . Ultrafast synthesis of Na₃V₂(PO₄)₃ cathode for high performance sodium-ion batteries. Chinese Chemical Letters, 2025, 36(2): 109643-. doi: 10.1016/j.cclet.2024.109643
9. [9]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
10. [10]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
11. [11]
  Hong-Tao Ji , Yu-Han Lu , Yan-Ting Liu , Yu-Lin Huang , Jiang-Feng Tian , Feng Liu , Yan-Yan Zeng , Hai-Yan Yang , Yong-Hong Zhang , Wei-Min He . Nd@C₃N₄-photoredox/chlorine dual catalyzed synthesis and evaluation of antitumor activities of 4-alkylated sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110568-. doi: 10.1016/j.cclet.2024.110568
12. [12]
  Qiuting Zhang , Fan Wu , Jin Liu , Hang Su , Yanhui Zhong , Zian Lin . Facile synthesis of single-crystal 3D covalent organic frameworks as stationary phases for high-performance liquid chromatographic separation. Chinese Chemical Letters, 2025, 36(8): 110649-. doi: 10.1016/j.cclet.2024.110649
13. [13]
  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
14. [14]
  Hang Wang , Qi Wang , Chuan-De Wu . Continuous synthesis of ammonia. Chinese Journal of Structural Chemistry, 2025, 44(3): 100437-100437. doi: 10.1016/j.cjsc.2024.100437
15. [15]
  Kun Wang , Tianxue Gong , Yaohuang Huang , Boyang Han , Hanxiao Yang , Pavlo O. Dral , Weiwei Fang . Bornylimidazo[1,5–a]pyridin-3-ylidene allylic Pd catalyst with optimal electronic and steric properties for synthesis of 3,3′-disubstituted oxindoles. Chinese Chemical Letters, 2025, 36(7): 110539-. doi: 10.1016/j.cclet.2024.110539
16. [16]
  Ya-Nan Yang , Zi-Sheng Li , Sourav Mondal , Lei Qiao , Cui-Cui Wang , Wen-Juan Tian , Zhong-Ming Sun , John E. McGrady . Metal-metal bonds in Zintl clusters: Synthesis, structure and bonding in [Fe₂Sn₄Bi₈]^3– and [Cr₂Sb₁₂]^3–. Chinese Chemical Letters, 2024, 35(8): 109048-. doi: 10.1016/j.cclet.2023.109048
17. [17]
  Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
18. [18]
  Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1150)
HTML views(45)

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