Citation:
Dong Wang, William E. Crowe. A facile approach to tricyclo[6.4.0.04,9]-dodecane framework[J]. Chinese Chemical Letters,
;2015, 26(2): 238-242.
doi:
10.1016/j.cclet.2014.11.003
-
The unusual tricyclo[6.4.0.04,9]dodecane framework was constructed in eight linear steps in 13% overall yield. An innovative strategy accessing the framework from bicyclo[3.3.1]nonanes was employed. The key steps involve a Robinson annulation, a base induced decarboxylation and epimerization in a single step, and an intramolecular alkylation.
-
-
-
[1]
[1] I. Uchida, T. Ando, N. Fukami, et al., The structure of vinigrol, a novel diterpenoid with antihypertensive and platelet aggregation-inhibitory activities, J. Org. Chem. 52 (1987) 5292-5293.
-
[2]
[2] T. Ando, Y. Tsurumi, N. Ohata, et al., Vinigrol, a novel antihypertensive and platelet aggregation inhibitory agent produced by a fungus, Virgaria nigra. I. Taxonomy, fermentation, isolation, physicochemical and biological properties, J. Antibiot. 41 (1988) 25-30.
-
[3]
[3] T. Ando, K. Yoshida, M. Okuhara, Vinigrol, a novel antihypertensive and platelet aggregation inhibitory agent produced by a fungus, Virgaria nigra. II. Pharmacological characteristics, J. Antibiot. 41 (1988) 31-35.
-
[4]
[4] H.G. Fritz, H. Henke, H. Musso, Asteranes. XI. 1,4-Dihydroxytricyclo[6.4.0.04,9]-dodecane-7,10-dione from furanophane, Chem. Ber. 107 (1974) 3164-3175.
-
[5]
[5] H. Buding, H. Musso, Optically active tricyclo[6.4.0.04,9]dodecane, Angew. Chem. Int. Ed. 17 (1978) 851.
-
[6]
[6] H. Buding, B. Deppisch, H. Musso, G. Snatzke, (R)-and (S)-tricyclo[6.4.0.04,9]-dodecane, Chem. Ber. 118 (1985) 4597-4612.
-
[7]
[7] H. Buding, B. Fuchs, H. Musso, Elimination of halogen from 1,4-dibromotricyclo[ 6.4.0.04,9]dodecane, Chem. Ber. 118 (1985) 4613-4615.
-
[8]
[8] E. Osawa, K. Aigami, Y. Inamoto, Application of force field calculations to organic chemistry. 6. Steric analysis of synthesis and structure of 1,4-dihydroxytricyclo[ 6.4.0.04,9]dodecane-7,10-dione. Dynamic conformational calculations of its hydrocarbon skeleton and related systems (bicyclo[3.3.1]nonane and bicyclo[ 3.3.2]decane), J. Chem. Soc., Perkin Trans. 2 (1979) 172-180.
-
[9]
[9] H.E. Winberg, F.S. Fawcett, W.E. Mochel, C.W. Theobald, Dimethylenedihydroheteroaromatic compounds and heterocyclophanes by 1, 6-Hofmann elimination reaction, J. Am. Chem. Soc. 82 (1960) 1428-1435.
-
[10]
[10] Y. Ito, S. Miyata, M. Nakatsuka, T. Saegusa, Fluoride-induced 1,6-elimination to pquinodimethane. A new preparative method for [2.2]paracyclophane,[2.2](2.5)furanophane and [2.2](2.5)thiophenophane, J. Org. Chem. 46 (1981) 1043-1044.
-
[11]
[11] P.S. Chen, C.H. Chou, Synthesis and chemistry of 2,5-dimethylene-2,5-dihydrofuran, J. Chin. Chem. Soc. (Taipei) 39 (1992) 251-255.
-
[12]
[12] K. Vandyck, B. Matthys, J. Van der Eycken, Synthesis and absolute configuration of (1S, 8S)-as-hydrindacene-1,8-diol as determined by the circular dichroism exciton chirality method, Tetrahedron Lett. 46 (2005) 75-78.
-
[13]
[13] L.A. Paquette, R. Guevel, S. Sakamoto, I.H. Kim, J. Crawford, Convergent enantioselective synthesis of vinigrol, an architecturally novel diterpenoid with potent platelet aggregation inhibitory and antihypertensive properties. 1. Application of anionic sigmatropy to construction of the octalin substructure, J. Org. Chem. 68 (2003) 6096-6107.
-
[14]
[14] L.A. Paquette, I. Efremov, Z. Liu, Exploratory studies aimed at a synthesis of vinigrol. 2. Attempts to exploit ring-closing metathesis for construction of the central cyclooctane belt, J. Org. Chem. 70 (2005) 505-509.
-
[15]
[15] L.A. Paquette, I. Efremov, Exploratory studies aimed at a synthesis of vinigrol. 3. Evaluation of a lactone bridge as a conformational lock, J. Org. Chem. 70 (2005) 510-513.
-
[16]
[16] L.A. Paquette, Z. Liu, I. Efremov, Exploratory studies aimed at a synthesis of vinigrol. 4. Probe of possible means for direct connection of the side arms and of ring-contraction alternatives, J. Org. Chem. 70 (2005) 514-518.
-
[17]
[17] J.E. Baldwin, Rules for ring closure, J. Chem. Soc. Chem. Commun. (1976) 734-736.
-
[18]
[18] J.E. Baldwin, M.J. Lusch, Rules for ring closure: application to intramolecular aldol condensations in polyketonic substrates, Tetrahedron 38 (1982) 2939-2947.
-
[19]
[19] D. Wang, W.E. Crowe, One-carbon bridge stereocontrol in Robinson annulations leading to bicyclo[3.3.1]nonanes, Org. Lett. 12 (2010) 1232-1235.
-
[20]
[20] X. Jiang, X. Xu, F. Qing, Design and concise synthesis of gem difluoromethylenated analogue of 7-epi-castanospermine, Chin. Chem. Lett. 25 (2014) 1115-1120.
-
[21]
[21] G.W. Kabalka, S. Yu, N.S. Li, Selective hydroboration of terminal alkenes in the presence of aldehydes and ketones, Tetrahedron Lett. 38 (1997) 5455-5458.
-
[22]
[22] CCDC-1012577 contains supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
-
[1]
-
-
-
[1]
Peng Guo , Shicheng Dong , Xiang-Gui Zhang , Bing-Bin Yang , Jun Zhu , Ke-Yin Ye . Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane (9-BBN) borates. Chinese Chemical Letters, 2025, 36(4): 110052-. doi: 10.1016/j.cclet.2024.110052
-
[2]
Ji-Ping Liao , Jiang Li , Wen-Jie Qin , Xiu-Mei Duan , Peng-Fei Wang , Jin-Ying Tian , Xiang Yuan , Pei-Cheng Zhang , Fei Ye , Ya-Nan Yang . Two racemic pairs of benzo bicyclo[3.3.1]/[4.2.1] nonene stilbenoid dimers from Heterosmilax yunnanensis and structural revision of syagrusin A. Chinese Chemical Letters, 2025, 36(9): 110687-. doi: 10.1016/j.cclet.2024.110687
-
[3]
Ze-Hong Zheng , Mu-Qiu Chen , Jin Zhou , Jie Wang , Yan-Rong Wei , Cheng Peng , Gu Zhan , Qian-Qian Yang , Bo Han . Diverse synthesis of bridged bicyclo[3.2.1]octa-2,6-diene and tricyclo[3.2.1.02,7]oct-3-ene frameworks via stepwise cascade reactions. Chinese Chemical Letters, 2025, 36(12): 111202-. doi: 10.1016/j.cclet.2025.111202
-
[4]
Jindian Duan , Xiaojuan Ding , Pui Ying Choy , Binyan Xu , Luchao Li , Hong Qin , Zheng Fang , Fuk Yee Kwong , Kai Guo . Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway. Chinese Chemical Letters, 2024, 35(10): 109565-. doi: 10.1016/j.cclet.2024.109565
-
[5]
Guang Xu , Cuiju Zhu , Xiang Li , Kexin Zhu , Hao Xu . Copper-catalyzed asymmetric [4+1] annulation of yne–allylic esters with pyrazolones. Chinese Chemical Letters, 2025, 36(4): 110114-. doi: 10.1016/j.cclet.2024.110114
-
[6]
Liu-Liang Mao , Yunyun Liu , Jie-Ping Wan . An update on the advances in chromone and the derivatives synthesis based on the key chromone annulation of o-hydroxyaryl enaminones. Chinese Chemical Letters, 2025, 36(7): 110784-. doi: 10.1016/j.cclet.2024.110784
-
[7]
Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
-
[8]
Xiaochun Liu , Gaoyan Chen , Xiaodong Yue , Chaoyue Wang , Xue-Xin Zhang , Xuecheng Ran , Yingxiao Zong , Junke Wang , Xicun Wang . A novel N-stable Co2P nano-catalyst for the synthesis of quinoxalines by annulation of alkynes and 1,2-diaminobenzenes. Chinese Chemical Letters, 2025, 36(8): 110707-. doi: 10.1016/j.cclet.2024.110707
-
[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]
Chen-Chang Cui , Shao-Qing Shi , Lu-Yao Wang , Feng Lin , Man-Su Tu , Wen-Juan Hao , Bo Jiang . Accessing polyarene-fused ten-membered lactams via oxidative N-heterocyclic carbene (NHC)-catalyzed high-order [7 + 3] annulation. Chinese Chemical Letters, 2025, 36(6): 110541-. doi: 10.1016/j.cclet.2024.110541
-
[11]
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
-
[12]
Wu-Yang Liu , Xin-Xiang Lei , Wen-Ji Wang , Jun-Mian Tian , Yu-Qi Gao , Jin-Ming Gao . Hyperforatone A, the 1,8-seco rearranged polycyclic polyprenylated acylphloroglucinol with a unique bicyclo[5.4.0]undecane core from Hypericum perforatum. Chinese Chemical Letters, 2025, 36(4): 110478-. doi: 10.1016/j.cclet.2024.110478
-
[13]
. . University Chemistry, 2024, 39(9): 0-0.
-
[14]
. Cover and Table of Contents for Vol.41 No. 9. Acta Physico-Chimica Sinica, 2025, 41(9): -.
-
[15]
. . University Chemistry, 2025, 40(9): 0-0.
-
[16]
Hanqi Zhang , Biao Gao , Yuanyuan Feng , Guijuan Zheng , Zhijun Liu , Lichun Kong , Junjun Liu , Haji Akber Aisa , Guangmin Yao . DFT calculations and dynamic NMR revealed the coalescent NMR phenomena of the 6/6/6/9 tetracyclic merosesquiterpenoids with an unprecedented 9,15-dioxatetracyclo[8.5.3.04,17.014,18]octadecane core skeleton. Chinese Chemical Letters, 2025, 36(9): 111234-. doi: 10.1016/j.cclet.2025.111234
-
[17]
Xinqiong Li , Guocheng Rao , Xi Peng , Chan Yang , Yanjing Zhang , Yan Tian , Xianghui Fu , Jia Geng . Direct detection of C9orf72 hexanucleotide repeat expansions by nanopore biosensor. Chinese Chemical Letters, 2024, 35(5): 109419-. doi: 10.1016/j.cclet.2023.109419
-
[18]
Yan Liu , Yang Wang , Jiayi Zhu , Xuxian Su , Xudong Lin , Liang Xu , Xiwen Xing . Employing pH-responsive RNA triplex to control CRISPR/Cas9-mediated gene manipulation in mammalian cells. Chinese Chemical Letters, 2024, 35(9): 109427-. doi: 10.1016/j.cclet.2023.109427
-
[19]
Guo-Ping Yin , Ya-Juan Li , Li Zhang , Ling-Gao Zeng , Xue-Mei Liu , Chang-Hua Hu . Citrinsorbicillin A, a novel homotrimeric sorbicillinoid isolated by LC-MS-guided with cytotoxic activity from the fungus Trichoderma citrinoviride HT-9. Chinese Chemical Letters, 2024, 35(8): 109035-. doi: 10.1016/j.cclet.2023.109035
-
[20]
Jiajun Wang , Guolin Yi , Shengling Guo , Jianing Wang , Shujuan Li , Ke Xu , Weiyi Wang , Shulai Lei . Computational design of bimetallic TM2@g-C9N4 electrocatalysts for enhanced CO reduction toward C2 products. Chinese Chemical Letters, 2024, 35(7): 109050-. doi: 10.1016/j.cclet.2023.109050
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(1067)
- HTML views(18)
Login In
DownLoad: