Citation: Dong Wang, William E. Crowe. A facile approach to tricyclo[6.4.0.0^4,9]-dodecane framework[J]. Chinese Chemical Letters, ;2015, 26(2): 238-242. doi: 10.1016/j.cclet.2014.11.003 shu

A facile approach to tricyclo[6.4.0.0^4,9]-dodecane framework

Dong Wang ^a,, ,
William E. Crowe ^b

a Longwood Biopharmaceuticals, Inc.
a Longwood Biopharmaceuticals, Inc.,Tianjin International Joint Academy of Biomedicine, Tianjin 300457, China;
2.
b Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA

Corresponding author: Dong Wang,
Received Date: 17 August 2014
Available Online: 21 October 2014
Fund Project: We thank Frank Fronczek (LSU) for assistance with X-ray crystallography. Financial support from TianJin Municipal Science and Technology Commission (No. 11ZCKFSY06200) is greatly acknowledged. (LSU)

The unusual tricyclo[6.4.0.0^4,9]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.
- Tricyclo[6.4.0.0^4,9]dodecane,
- Vinigrol,
- Robinson annulation,
- Bicyclo[3.3.1]nonane
1. [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]
  [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]
  [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]
  [4] H.G. Fritz, H. Henke, H. Musso, Asteranes. XI. 1,4-Dihydroxytricyclo[6.4.0.0^4,9]-dodecane-7,10-dione from furanophane, Chem. Ber. 107 (1974) 3164-3175.
5. [5]
  [5] H. Buding, H. Musso, Optically active tricyclo[6.4.0.0^4,9]dodecane, Angew. Chem. Int. Ed. 17 (1978) 851.
6. [6]
  [6] H. Buding, B. Deppisch, H. Musso, G. Snatzke, (R)-and (S)-tricyclo[6.4.0.0^4,9]-dodecane, Chem. Ber. 118 (1985) 4597-4612.
7. [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [17] J.E. Baldwin, Rules for ring closure, J. Chem. Soc. Chem. Commun. (1976) 734-736.
18. [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]
  [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]
  [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]
  [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]
  [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]
  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
2. [2]
  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
3. [3]
  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
4. [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. [5]
  . . University Chemistry, 2024, 39(9): 0-0.
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  Hao GUO , Tong WEI , Qingqing SHEN , Anqi HONG , Zeting DENG , Zheng FANG , Jichao SHI , Renhong LI . Electrocatalytic decoupling of urea solution for hydrogen production by nickel foam-supported Co₉S₈/Ni₃S₂ heterojunction. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2141-2154. doi: 10.11862/CJIC.20240085
11. [11]
  Yuan Teng , Zichun Zhou , Jinghua Chen , Siying Huang , Hongyan Chen , Daibin Kuang . Dual atom-bridge effect promoting interfacial charge transfer in 2D/2D Cs₃Bi₂Br₉/BiOBr epitaxial heterojunction for efficient photocatalysis. Chinese Chemical Letters, 2025, 36(2): 110430-. doi: 10.1016/j.cclet.2024.110430
12. [12]
  Cheng PENG , Jianwei WEI , Yating CHEN , Nan HU , Hui ZENG . First principles investigation about interference effects of electronic and optical properties of inorganic and lead-free perovskite Cs₃Bi₂X₉ (X=Cl, Br, I). Chinese Journal of Inorganic Chemistry, 2024, 40(3): 555-560. doi: 10.11862/CJIC.20230282

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(585)
HTML views(11)

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

A facile approach to tricyclo[6.4.0.04,9]-dodecane framework

Metrics

通讯作者: 陈斌, bchen63@163.com

A facile approach to tricyclo[6.4.0.0^4,9]-dodecane framework