研究简报

Lucidone和Methyl Lucidone的简洁合成

  • 刘武 ,
  • 肖粉粉 ,
  • 胡向东
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  • 西北大学化学与材料科学学院教育部合成与天然功能分子重点实验室 西安 710069

收稿日期: 2012-12-31

  修回日期: 2013-01-28

  网络出版日期: 2013-02-05

基金资助

国家自然科学基金(No. 21002078)资助项目.

Concise Synthesis of Lucidone and Methyl Lucidone

  • Liu Wu ,
  • Xiao Fenfen ,
  • Hu Xiangdong
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  • Department of Chemistry & Material Science, Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education of China, Northwest University, Xi'an 710069

Received date: 2012-12-31

  Revised date: 2013-01-28

  Online published: 2013-02-05

Supported by

Project supported by the National Natural Science Foundation of China (No. 21002078).

摘要

报道了lucidone和methyl lucidone的简洁合成, 其关键步骤为方酸二甲酯的还原/重排“一锅”反应和单甲氧基环丁烯二酮的达森/扩环反应. Lucidone的合成经过两步反应以46%的总收率实现. Methyl lucidone的合成经过三步反应以43%的总收率完成.

本文引用格式

刘武 , 肖粉粉 , 胡向东 . Lucidone和Methyl Lucidone的简洁合成[J]. 有机化学, 2013 , 33(07) : 1587 -1590 . DOI: 10.6023/cjoc201212051

Abstract

The concise synthesis of lucidone and methyl lucidone is reported. The key steps include the "one-pot" reduction/rearrangement of dimethyl squarate and the Darzens/ring expansion of the monomethoxyl cyclobutenedione. The synthesis of lucidone was finished in two steps and 46% total yield. And the synthesis of methyl lucidone had been reached in three steps and 43% overall yield.

参考文献

[1] (a) Lee, H. H.; Tan, C. H. J. Chem. Soc. 1965, 4, 2743. (b) Liu, S. Y.; Hisada, S.; Inagaki, I. Phytochemistry 1973, 12, 233. (c) Liu, S. Y.; Hisada, S.; Inagaki, I. Phytochemistry 1973, 12, 472. (d) Takai, M.; Liu, S. Y.; Ogihara, Y.; Iitaka, Y. Chem. Pharm. Bull. 1977, 25, 1404.
[2] Ng, S.; Lee, H. H.; Bennett, G. J. Magn. Reson. Chem. 1990, 28, 337.
[3] (a) Wang, S. Y.; Lan, X. Y.; Xiao, J. H.; Yang, J. C.; Kao, Y. T.; Chang, S. T. Phytother. Res. 2008, 22, 213. (b) Senthil Kumar, K. J.; Hsieh, H. W.; Wang, S. Y. Int. Immunopharmacol. 2010, 10, 385. (c) Senthil Kumar, K. J.; Wang, S. Y. Planta Med. 2009, 75, 494
[4] (a) Senthil Kumar, K. J.; Yang, J. C.; Chu, F. H.; Chang, S. T.; Wang, S. Y. Phytother. Res. 2010, 24, 1158. (b) Kim, G. O.; Ko, R. G.; Kang, M. C.; Jin, Y. J.; Han, J. H.; Choi, H. M.; Ko, G. H.; Kim, B. S.; Jin, H. G.; Jin, G. H.; Jung, Y. H.; Lee, N. H. KR 2011032931, 2011 [Chem. Abstr. 2011, 154, 468758]. (c) Kim, G. O.; Ko, R. K.; Jin, Y. J.; Kang, M. C.; Han, J. H.; Choi, H. M.; Ko, K. H.; Kim, B. S.; Jin, H. K.; Jin, K. H. WO 2010027221, 2010[Chem. Abstr. 2010, 152, 343066].
[5] Senthil Kumar, K. J.; Liao, J. W.; Xiao, J. H.; Gokila, V. M.; Wang, S. Y. Toxicol. In Vitro 2012, 26, 700.
[6] (a) Wang, S. Y. JP 2012012343, 2012 [Chem. Abstr. 2012, 156, 167733]. (b) Wang, S. Y. DE 102010025864, 2012 [Chem. Abstr. 2012, 156, 132567]. (c) Wang, S. Y. US 20110319495, 2011 [Chem. Abstr. 2011, 156, 84542]. (d) Wang, S. Y. CN 102274209, 2011 [Chem. Abstr. 2011, 156, 65637].
[7] (a) Oh, H. M.; Choi, S. K.; Lee, J. M.; Lee, S. K.; Kim, H. Y.; Han, D. C.; Kim, H. M.; Son, K. H.; Kwon, B. M. Bioorg. Med. Chem. 2005, 13, 6182. (b) Kwon, B. M.; Son, K. H.; Han, D. C.; Choi, S. K.; Oh, H. M. KR 2006104555, 2006 [Chem. Abstr. 2007, 146, 190351].
[8] Cui, Y.; Wu, J.; Jung, S. C.; Kim, G. O.; Ko, R. K.; Lee, H. J.; Yoo, E. S.; Kang, H. K.; Suk, K.; Eun, S. Y. Eur. J. Pharmacol. 2012, 690, 4.
[9] Choi, Y. H.; Kwon, S. Y.; Kim, J. H.; Beak, N. I.; Choi, G. J.; Cho, K. Y.; Lee, B. M. Han'guk Nonghwa Hakhoechi 2003, 46, 151.
[10] Lee, H. H.; Que, Y. T. J. Chem. Soc., Perkin Trans. 1 1985, 453.
[11] (a) Bose, G.; Langer, P. Synlett 2005, 1021. (b) Freifeld, I.; Bose, G.; Eckardt, T.; Langer, P. Eur. J. Org. Chem. 2007, 2, 351.
[12] Clemo, N. G.; Gedge, D. R.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1981, 1448.
[13] (a) Li X. C.; Ferreira D.; Jacob M. R.; Zhang Q.; Khan, S. I.; ElSohly, H. N.; Nagle, D. G.; Smillie, T. J.; Khan, I. A.; Walker, L. A.; Clark, A. M. J. Am. Chem. Soc. 2004, 126, 6872. (b) Tan, H.; Zheng, C.; Liu, Z.; Wang, D. Z. Org. Lett. 2011, 13, 2192.
[14] Xiao, F.; Liu, W.; Wang, Y.; Zhang, Q.; Li, X.; Hu, X. Asian J. Org. Chem. 2013, 2, 216.
[15] Heerding, J. M.; Moore, H. W. J. Org. Chem. 1991, 56, 4048.
[16] (a) Liebeskind, L. S.; Fengl, R. W.; Wirtz, K. R.; Shawe, T. T. J. Org. Chem. 1988, 53, 2482. (b) Liebeskind, L. S. Tetrahedron 1989, 45, 3053. (c) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149.
[17] Lee, H. H. Ttrahedron Lett. 1968, 40, 4243.
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