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
-
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.
-
Keywords:
- Synthesis,
- Furo[3,2-a]carbazole,
- Transamination
-
-
[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] C. Ito, H. Furukawa, New carbazole alkaloids from Murraya euchrestifolia Hayata, Chem. Pharm. Bull. 38 (1990) 1548-1550.
-
[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] 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] 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] 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] S. Ohta, M. Okamoto, Synthesis of carbonyl compouds via biogenetic-type transamination reaction, Synthesis 9 (1982) 756-758.
-
[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] 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] 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] C.J. Pearce, T.W. Doyle, S. Forenza, et al., The biosynthetic origins of rebeccamycin, J. Nat. Prod. 51 (1988) 937-940.
-
[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] 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] 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] 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]
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
-
[3]
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
-
[4]
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
-
[5]
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
-
[6]
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
-
[7]
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
-
[8]
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
-
[9]
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
-
[10]
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
-
[11]
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
-
[12]
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
-
[13]
Caili Yang , Tao Long , Ruotong Li , Chunyang Wu , Yuan-Li Ding . Pseudocapacitance dominated Li3VO4 encapsulated in N-doped graphene via 2D nanospace confined synthesis for superior lithium ion capacitors. Chinese Chemical Letters, 2025, 36(2): 109675-. doi: 10.1016/j.cclet.2024.109675
-
[14]
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
-
[15]
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
-
[16]
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
-
[17]
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
-
[18]
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
-
[19]
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
-
[20]
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
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(581)
- HTML views(24)