(1aRS,7aRS)-7-羟基氨亚基-1,1a,7,7a-4H-丙环骈[b]色烯-1a-甲酸乙酯及其衍生物的有效全合成
收稿日期: 2015-02-24
修回日期: 2015-03-17
网络出版日期: 2015-03-24
基金资助
国家自然科学基金(No.81172982)资助项目.
An Efficient Total Synthesis of Ethyl 7-(Hydroxyimino)cyclopropa-[b]chromen-1a-carboxylate and Their Derivatives
Received date: 2015-02-24
Revised date: 2015-03-17
Online published: 2015-03-24
Supported by
Project supported by the National Natural Science Foundation of China (No.81172982).
许男徽 , 陈河如 . (1aRS,7aRS)-7-羟基氨亚基-1,1a,7,7a-4H-丙环骈[b]色烯-1a-甲酸乙酯及其衍生物的有效全合成[J]. 有机化学, 2015 , 35(5) : 1033 -1039 . DOI: 10.6023/cjoc201502029
Ethyl 7-(hydroxyimino)cyclopropa[b]chromen-1a-carboxylate and their derivatives have been synthesized through directed acylation, intramolecular cyclization under the catalysis of iodine, cyclopropanation, esterification and oximation by using phenol and maleic anhydride as starting materials. In the current invetigation, the construction of chromone scaffold was improved and the cyclopropanation upon the treatment of Corey's dimethyloxosulfonium methylide was applied. The structures of all the intermediates and final products were confirmed by 1H NMR, 13C NMR, and MS, respectively. The overall yields of these 5-step procedures were 20.1%~29.5%.
Key words： mGluR modulators; total synthesis; iodonium; cyclopropanation
[1] Annoura, H.; Fukunaga, A.; Uesugi, M.; Tatsuoka, T.; Horikawa, Y. Bioorg. Med. Chem. Lett. 1996, 6, 763.
[2] Maj, M.; Bruno, V.; Dragic, Z.; Yamamoto, R.; Battaglia, G.; Inderbitzin, W.; Stoehr, N.; Stein, T.; Gasparini, F.; Vranesic, I.; Kuhn, R.; Nicoletti, F.; Flor, P. J. Neuropharmacology 2003, 45, 895.
[3] Marino, M. J.; Williams, D. L. Jr.; O'Brien, J. A.; Valenti, O.; McDonald, T. P.; Clements, M. K.; Wang, R.; DiLella, A. G.; Hess, J. F.; Kinney, G. G.; Conn, P. J. Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 13668.
[4] Conn, P. J.; Pin, J.-P. Annu. Rev. Pharmacol. Toxicol. 1997, 37, 205.
[5] Hopkins, C. R.; Lindsley, C. W.; Niswender, C. M. Future Med. Chem. 2009, 1, 501.
[6] Lindsley, C. W.; Niswender, C. M.; Engers, D. W.; Hopkins, C. R. Curr. Top. Med. Chem. (Sharjah, United Arab Emirates) 2009, 9, 949.
[7] Iacovelli, L.; Arcella, A.; Battaglia, G.; Pazzaglia, S.; Aronica, E.; Spinsanti, P.; Caruso, A.; De Smaele, E.; Saran, A.; Gulino, A.; D'Onofrio, M.; Giangaspero, F.; Nicoletti, F. J. Neurosci 2006, 26, 8388.
[8] Canudas, A. M.; Di Giorgi-Gerevini, V.; Iacovelli, L.; Nano, G.; D'Onofrio, M.; Arcella, A.; Giangaspero, F.; Busceti, C.; Ricci-Vitiani, L.; Battaglia, G.; Nicoletti, F.; Melchiorri, D. J. Neurosci. 2004, 24, 10343.
[9] Stachowicz, K.; Klak, K.; Klodzinska, A.; Chojnacka-Wojcik, E.; Pilc, A. Eur. J. Pharmacol. 2004, 498, 153.
[10] Marino, M. J.; Hess, J. F.; Liverton, N. Curr. Top. Med. Chem. (Sharjah, United Arab Emirates) 2005, 5, 885.
[11] Williams, R.; Zhou, Y.; Niswender, C. M.; Luo, Q.; Conn, P. J.; Lindsley, C. W.; Hopkins, C. R. ACS Chem. Neurosci. 2010, 1, 411.
[12] Blatt, A. H. Org. React. 1942, 1, 342.
[13] Brown, R. S.; Nagorski, R. W.; Bennet, A. J.; McClung, R. E. D.; Aarts, G. H. M.; Klobukowski, M.; McDonald, R.; Santarsiero, B. D. J. Am. Chem. Soc. 1994, 116, 2448.
[14] (a) Godoi, B.; Schumacher, R. F.; Zeni, G. Chem. Rev. 2011, 111, 2937. (b) Maloney, D. J.; Hecht, S. M. Org. Lett. 2005, 7, 1097. (c) Khan, M. S. Y.; Sharma, P. Indian J. Chem., Sect. B 1993, 32, 817. (d) Kitagawa, M.; Yamamoto, K.; Katakura, S.; Kanno, H.; Yamada, K. Chem. Pharm. Bull. 1991, 39, 2681.
[15] (a) Dean, F. M.; Johnson, R. S. J. Chem. Soc., Perkin Trans. 1 1981, 224; (b) Dicker, I. D.; Shipman, J.; Suschitzky, J. L. J. Chem. Soc., Perkin Trans. 1 1984, 487.
[16] Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353.
[17] Saunders, D.; Warrington, B. H. J. Labelled Compd. Radiopharm. 1985, 22, 869.
[18] Chimenti, F.; Fioravanti, R.; Bolasco, A.; Chimenti, P.; Secci, D.; Rossi, F.; Yanez, M.; Orallo, F.; Ortuso, F.; Alcaro, S.; Cirilli, R.; Ferretti, R.; Sanna, M. L. Bioorg. Med. Chem. 2010, 18, 1273.
[19] Dhaon, M. K.; Olsen, R. K.; Ramasamy, K. J. Org. Chem. 1982, 47, 1962.
[20] Flick, A. C.; Caballero, M. J. A.; Lee, H. I.; Padwa, A. J. Org. Chem. 2010, 75, 1992.
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