Synthesis of Two Coumarins Isolated from Aster praealtus
Bo Wang
State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Key Laboratory of Green Chemical Technology of College of Heilongjiang Province, School of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China
Search for more papers by this authorHuijun Chen
State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Yikang Wu
State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Yikang Wu, State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Bo Liu, Key Laboratory of Green Chemical Technology of College of Heilongjiang Province, School of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China
Search for more papers by this authorCorresponding Author
Bo Liu
Key Laboratory of Green Chemical Technology of College of Heilongjiang Province, School of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China
Yikang Wu, State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Bo Liu, Key Laboratory of Green Chemical Technology of College of Heilongjiang Province, School of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China
Search for more papers by this authorBo Wang
State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Key Laboratory of Green Chemical Technology of College of Heilongjiang Province, School of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China
Search for more papers by this authorHuijun Chen
State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Yikang Wu
State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Yikang Wu, State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Bo Liu, Key Laboratory of Green Chemical Technology of College of Heilongjiang Province, School of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China
Search for more papers by this authorCorresponding Author
Bo Liu
Key Laboratory of Green Chemical Technology of College of Heilongjiang Province, School of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China
Yikang Wu, State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Bo Liu, Key Laboratory of Green Chemical Technology of College of Heilongjiang Province, School of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China
Search for more papers by this authorAbstract
Two coumarins isolated from Aster praealtus were synthesized via a direct coupling of the corresponding cyclohexyl carbinol with a coumarin-derived aryl bromide or iodide, a very difficult etherification due to the excess steric congestion around the carbinol and the low reactivity of the aryl halide that frustrated many seemingly feasible protocols. Unequivocal 1H and 13C NMR data for these compounds were thus made available for the first time. Uncertainty and errors in 1H and 13C NMR data in previous reports are also eliminated and revealed, respectively.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
| Filename | Description |
|---|---|
| cjoc_201500295_sm_suppl.pdf420.7 KB | suppl |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1 Chen, H.-J.; Wu, Y.-K.. Org. Lett., 2015, 17, 592.
- 2a Liu, D.-A.; Dong, Z.-J.; Wang, F.; Liu, J.-K.. Tetrahedron Lett., 2010, 51, 3152.
- 2b Chokpaiboon, S.; Sommit, D.; Teerawatananond, T.; Muangsin, N.; Bunyapaiboonsri, T.; Pudhom, K.. J. Nat. Prod., 2010, 73, 1005.
- 2c Liu, D.-Z.; Luo, M.-H.. Fitoterapia, 2010, 81, 1205.
- 2d Li, H.; Huang, H.; Shao, C.; Huang, H.; Jiang, J.; Zhu, X.; Liu, Y.; Liu, L.; Lu, Y.; Li, M.; Lin, Y.; She, Z.. J. Nat. Prod., 2011, 74, 1230.
- 2e Chokpaiboon, S.; Sommit, D.; Bunyapaiboonsri, T.; Matsubara, K.; Pudhom, K.. J. Nat. Prod., 2011, 74, 2290.
- 2f Wibowo, M.; Prachyawarakorn, V.; Aree, T.; Wiyakrutta, S.; Mahidol, C.; Ruchirawat, S.; Kittakoop, P.. Eur. J. Org. Chem., 2014, 3976.
- 2g For use of merulin A for the treatment of African sleeping sickness, see: Navarro, G.; Chokpaiboon, S.; De Muylder, G.; Bray, W. M.; Nisam, S. C.; McKerrow, J. H.; Pudhom, K.; Linington, R. G.. PLoS One, 2012, 7, e46172.
- 2h Linington, R.; Navarro, G.; Pudhom, K.; McKerrow, J., WO 2013019686 A2 Chem. Abstr., 2013, 158, 302292.
- 3 The relative configurations for 4 and 5 depicted in this work are adopted from those in the literature (ref 5 below), which presumably were deduced on the basis of the single crystal X-ray crystallographic analysis of 6 (Praealtin A) isolated at the same time.
- 4 Bohlmann, F.; Zdero, C.; Kapteyn, H.. Liebig. Ann. Chem., 1968, 717, 186.
- 5 Wilzer, K. A.; Fronczek, F. R.; Urbatsch, L. E.; Fischer, N. H.. Phytochemistry, 1989, 28, 1729.
- 6 Coates, R. M.; Melvin, L. S., Jr.. Tetrahedron, 1970, 26, 5699.
- 7 Aziz, M.; Rouessac, F.. Tetrahedron, 1988, 44, 101 (in Frehch. Cf. the 1H NMR data for the compounds "8 (1)" and "8 (2)" therein). It appears that the data sets therein were switched by mistake-while the planar structure for the"8 (2)" matched the 4 in this work, the corresponding data were given for the exocyclic alkenic isomer "8 (1)" therein. For detailed tabular comparisons, see: the Supporting Information.
- 8For an epimer of 4 (with the relative configuration depicted as anti), see:
- 8a Bohlmann, F.; Gerke, T.; King, R. M.; Robinson, H.. Liebig. Ann. Chem., 1983, 714 (the compound 6 therein, without any accompanying data).
- 8b Almahy, H. A.; Alagimi, A. A.. Arabian J. Chem., 2012, 5, 241.
- 8c For importance and bioactivities of some oxygenated coumarins, see e.g.: Riveiro, M. E.; De Kimpe, N.; Moglioni, A.; Vazquez, R.; Monczor, F.; Shayo, C.; Davio, C.. Curr. Med. Chem., 2010, 17, 1325.
- 8d Riveiro, M. E.; Maes, D.; Vazquez, R.; Vermeulen, M.; Mangelinckx, S.; Jacobs, J.; Debenedetti, S.; Shayo, C.; De Kimpe, N.; Davio, C.. Biorg. Med. Chem., 2009, 17, 6547.
- 8e Maes, D.; Vervisch, S.; Debenedetti, S.; Davio, C.; Mangelinckx, S.; Giubellina, N.; De Kimpe, N.. Tetrahedron, 2005, 61, 2505.
- 9 Bovolenta, M.; Castronovo, F.; Vadala, A.; Zanoni, G.; Vidari, G.. J. Org. Chem., 2004, 69, 8959.
- 10a Belluti, F.; Perozzo, R.; Lauciello, L.; Colizzi, F.; Kostrewa, D.; Bisi, A.; Gobbi, S.; Rampa, A.; Bolognesi, M. L.; Recanatini, M.; Brun, R.; Scapozza, L.; Cavalli, A.. J. Med. Chem., 2013, 56, 7516.
- 10b Reisch, J.; Wickramasinghe, A.; Kumar, V.. Monatshefte Chem., 1988, 119, 1333.
- 11a Sevestre, A.; Helaine, V.; Guyot, G.; Martin, C.; Hecquet, L.. Tetrahedron Lett., 2003, 44, 827.
- 11b Clarke, D. J.; Robinson, R. S.. Tetrahedron, 2002, 58, 2831.
- 11c Kosiova, I.; Kovackova, S.; Kois, P.. Tetrahedron, 2007, 6, 312.
- 11d Tobe, M.; Isobe, Y.; Goto, Y.; Obara, F.; Tsuchiya, M.; Matsui, J.; Hirota, K.; Hayashi, H.. Bioorg. Med. Chem., 2000, 8, 2037.
- 11e Liu, M.-M.; Chen, X.-Y.; Huang, Y.-Q.; Feng, P.; Guo, Y.-L.; Yang, G.; Chen, Y.. J. Med. Chem., 2014, 57, 9343.
- 12 Palucki, M.; Wolfe, J. P.; Buchwald, S. L.. J. Am. Chem. Soc., 1997, 119, 3395.
- 13a For synthesis of 8 from m-bromo-phenol and malic acid, see: Belluti, F.; Perozzo, R.; Lauciello, L.; Colizzi, F.; Kostrewa, D.; Bisi, A.; Gobbi, S.; Rampa, A.; Bolognesi, M. L.; Recanatini, M.; Brun, R.; Scapozza, L.; Cavalli, A.. J. Med. Chem., 2013, 56, 7516 (where NMR data for 8 were incompatible with those in ref 12b).
- 13b Mitteilung, K.; Reisch, J.; Rosenthal, B. H. W.. Monatshefte Chem., 1987, 118, 871.
- 13c For an alternative route to 8 from 7, see: Thompson, A. L. S.; Kabalka, G. W.; Akula, M. R.; Huffman, J. W.. Synthesis, 2005, 547.
- 14 Vorgushin, A. V.; Huang, X.; Buchwald, S. L.. J. Am. Chem. Soc., 2005, 127, 8146.
- 15 Ma, D.; Cai, Q.. Acc. Chem. Res., 2008, 41, 1450.
- 16 Wolter, M.; Nordmann, G.; Job, G. E.; Buchwald, S. L.. Org. Lett., 2002, 4, 973.
- 17 Niu, J.; Guo, P.; Kang, J.; Li, Z.; Xu, J.; Hu, S.. J. Org. Chem., 2009, 74, 5075.
- 18 Bassoli, A.; Borgonovo, G.; Busnelli, G.; Morini, G.. Eur. J. Org. Chem., 2006, 1656.
- 19 Liu, H.-J.; Yip, J.. Tetrahedron Lett., 1997, 38, 2253.
- 20a Morriello, G. J.; Devita, R. J.; Moyes, C. R.. WO 2008057336 A2 Chem. Abstr., 2008, 148, 561711.
- 20b Such plans were rather common in synthesis of coumarins, see e.g.: Maes, D.; Riveiro, M. E.; Shayo, C.; Davio, C.; Debenedetti, S.; De Kimpe, N.. Tetrahedron, 2008, 64, 4438.
- 20c Gong, D.-H.; Li, C.-Z.; Yuan, C.-Y.. Chin. J. Chem., 2001, 19, 517.
- 21 Attachment of 3 or the epoxy (of the tri-substituted CC double bond) geraniol onto coumarin core via Mitsunobu reaction with 7 was unsuccessful.
- 22 Vatèle, J.-M.. Tetrahedron Lett., 2006, 47, 715.
- 23 The ref 5 above did not provide any data for 4, only referred to the ref 4 above.
- 24 Thakar, K. A.; Goswami, D. D.. J. Ind. Chem. Soc., 1972, 49, 707.
- 25 Bovolenta, M.; Castronovo, F.; Vadalà, A.; Zanoni, G.; Vidari, G.. J. Org. Chem., 2004, 69, 8959.
