Synthesis of Muricatacin and 6-Acetoxy-5-hexadecanolide Isomers from Pent-4-ynoic Acid and Hex-5-ynoic Acid

doi:10.6023/cjoc201408035

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 152-158.DOI: 10.6023/cjoc201408035 Previous Articles Next Articles

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由4-戊炔酸和5-己炔酸合成Muricatacin和6-乙酰氧基十六碳烷酸-5-内酯立体异构体

董宏波, 杨明艳, 张晓腾, 王明安

中国农业大学应用化学系北京 100193

收稿日期:2014-08-28 修回日期:2014-09-23 发布日期:2014-09-25
通讯作者: 王明安 E-mail:wangma@cau.edu.cn
基金资助:
国家自然科学基金(No. 21172254)和国家高技术研究与发展计划(863计划, No. 2011AA10A202)资助项目.

Synthesis of Muricatacin and 6-Acetoxy-5-hexadecanolide Isomers from Pent-4-ynoic Acid and Hex-5-ynoic Acid

Dong Hongbo, Yang Mingyan, Zhang Xiaoteng, Wang Ming'an

Department of Applied Chemistry, China Agricultural University, Beijing 100193

Received:2014-08-28 Revised:2014-09-23 Published:2014-09-25
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21172254) and the National Hi-Tech R&D Program of China (863 Program, No. 2011AA10A202).

1. Synthesis of Muricatacin and 6-Acetoxy-5-hexadecanolide Isomers from Pent-4-ynoic Acid and Hex-5-ynoic Acid.PDF(354KB)

Abstract

The four isomers of 6-acetoxy-5-hexadecanolide and muricatacin were synthesized in 6～7 steps through pent- 4-ynoic acid and hex-5-ynoic acid as raw materials and Sharpless asymmetric dihydroxylation as the key step in overall yields of 33.5%～54.6%. Their structures were confirmed by ¹H NMR, ¹³C NMR, HR-ESI-MS data and X-ray diffraction. The absolute configuration of (-)-epi-muricatacin was also ascertained by X-ray diffraction analysis.

Key words: muricatacin, 6-acetoxy-5-hexadecanolide, sharpless asymmetric dihydroxylation, synthesis

Cite this article

Dong Hongbo, Yang Mingyan, Zhang Xiaoteng, Wang Ming'an. Synthesis of Muricatacin and 6-Acetoxy-5-hexadecanolide Isomers from Pent-4-ynoic Acid and Hex-5-ynoic Acid[J]. Chin. J. Org. Chem., 2015, 35(1): 152-158.

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[1] Rieser, M. J.; Kozlowski, J. F.; Wood, K. V.; McLaughlin, J. L. Tetrahedron Lett. 1991, 32, 1137.
[2] Murcia, M. C.; Navarro, C.; Moreno, A.; Csaky A. G. Curr. Org. Chem. 2009, 14, 15.
[3] Bermejo, A.; Figadere, B.; Zafra-Polo, M. C.; Barrachina, I.; Estornell, E.; Cortes, D. Nat. Prod. Rep., 2005, 22, 269.
[4] Laurence, B. R.; Pickett, J. A. J. Chem. Soc., Chem. Commun. 1982, 59.
[5] Sakakibara, M.; Ikeshoji, T.; Machiya K., Ichimoto, I. Eisei Dobutsu 1984, 35, 401.
[6] Olagbemiro, T. O.; Birkett, M. A.; Mordue, J. M.; Pickett J. A. J. Agric. Food Chem. 1999, 47, 3411.
[7] Mao, Y.; Xu, X. Z.; Xu, W.; Ishida, Y.; Leal, W. S.; Ames, J. B.; Clardy, J. Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 19102.
[8] Yu, H.; Zhao, X.; Feng, X. L.; Chen, X. C.; Borowiak-Palen, E.; Huang, X. R. J. Biomol. Struct. Dyn. 2013, 31, 485.
[9] Chu, W. T.; Zhang, J. L.; Zheng, Q. C.; Chen, L.; Wu, Y. J.; Xue, Q.; Zhang, H. X. J. Mol. Model. 2013, 19, 1301.
[10] (a) Gonzalez, M.; Gandara, Z.; Covelo, B.; Gomez, G.; Fall, Y. Tetrahedron Lett. 2011, 52, 5983. (b) Gonzalez, M.; Gandara, Z.; Pazos, G.; Gomez, G.; Fall, Y. Synthesis 2013, 45, 625. (c) Singh, S.; Guiry, P. J. Eur. J. Org. Chem. 2009, 1896. (d) Park, Y.; Tae, J. Synthesis 2010, 3627. (e) Das, S.; Mishra A. K.; Kumar, A.; Al Ghamdi, A. A. K.; Yadav, J. S. Carbohydr. Res. 2012, 358, 7.
[11] Dong, H. B.; Yang, M. Y.; Liu, B.; Wang, M. A. J. Asian Nat. Prod. Res. 2014, 16, 847.
[12] Dong, H. B.; Yang, M. Y.; Zhang, X. T.; Wang, M. A. Tetrahedron: Asymmetry 2014, 25, 610.
[13] (a) Lin, G. Q.; Xu, H. J.; Wu, B. C.; Guo, G. Z.; Zhou, W. S. Tetrahedron Lett. 1985, 26, 1233. (b) Lin, G. Q.; Xu, H. J.; Wu, B. C.; Guo, G. Z.; Zhou, W. S. Acta Chim. Sinica 1986, 44, 597 (in Chinese). (林国强, 徐海剑, 吴碧琪, 郭广忠, 周维善, 化学学报, 1986, 44, 597.) (c) Lin, G. Q.; Jiang, Y. Y.; Guo, G. Z.; Xia, K. M. Acta Chim. Sinica 1987, 45, 602 (in Chinese). (林国强, 蒋彦颖, 郭广忠, 夏克敏, 化学学报, 1987, 45, 602.) (d) Zhou, W. S.; Cheng, J. F.; Lin G. Q. Acta Chim. Sinica 1988, 46, 274 (in Chinese). (周维善, 程杰飞, 林国强, 化学学报, 1988, 46, 274.)
[14] (a) Ito, M.; Osaku, A.; Shiibashi, A.; Ikariya, T. Org. Lett. 2007, 9, 1821. (b) Ahmed, M. M.; Cui, H.; O'Doherty, G. A. J. Org. Chem. 2006, 71, 6686. (c) Lohray, B. B.; Venkateswarlu, S. Tetrahedron: Asymmetry 1997, 8, 633. (d) Couladouros E. A., Mihou A. P. Tetrahedron Lett. 1999, 40, 4861. (e) Yao, Z. J.; Zhang, Y. B.; Wu, Y. L. Acta Chim. Sinica 1992, 50, 901 (in Chinese). (姚祝军, 张一兵, 吴毓林, 化学学报, 1992, 50, 901.) (f) Wu, W. L.; Wu, Y. L. J. Carbohydr. Chem. 1991, 10, 279.
[15] Hurem, D.; Dudding, T. RSC Adv. 2014, 4, 15552. Gonzalez, M.; Gandara, Z.; Martínez, A.; Gomez, G.; Fall, Y. Synthesis 2013, 45, 1693.

由4-戊炔酸和5-己炔酸合成Muricatacin和6-乙酰氧基十六碳烷酸-5-内酯立体异构体

Synthesis of Muricatacin and 6-Acetoxy-5-hexadecanolide Isomers from Pent-4-ynoic Acid and Hex-5-ynoic Acid

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