SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2014 , Vol. 34 >Issue 11: 2350 - 2353

DOI: https://doi.org/10.6023/cjoc201406005

Notes

Total Synthesis of 3,7-Dimethyl-7-hydroxy-2-octen-1,6-olide and (E)-6,7-Dihydroxy-3,7-dimethyl-2-octenic Acid

  • Dong Hongbo ,
  • Yang Mingyan ,
  • Tang Bo ,
  • Wang Mingan
Expand
  • Department of Applied Chemistry, China Agricultural University, Beijing 100193

Received date: 2014-06-05

  Revised date: 2014-07-02

  Online published: 2014-07-15

Supported by

Project supported by the National Key Technologies R&D Program (No.2011BAE06B04) and the National Natural Science Foundation of China (No.21172254).

Fold

Abstract

The total synthesis of 3,7-dimethyl-7-hydroxy-2-octen-1,6-olide and (E)-6,7-dihydroxy-3,7-dimethyl-2-octenic acid were carried out though Wittig reaction, hydrolyzation, epoxidation and intramolecular cyclization or ring-opening in overall yields of 6.4% and 23.7% using 6-methyl-5-hepten-2-one as raw materials, and their structures were characterized by 1H NMR, 13C NMR and ESI-MS spectral data.

Key words： 3,7-dimethyl-7-hydroxy-2-octen-1,6-olide; (E)-6,7-dihydroxy-3,7-dimethyl-2-octenic acid; total synthesis; natural product

Cite this article

Dong Hongbo , Yang Mingyan , Tang Bo , Wang Mingan . Total Synthesis of 3,7-Dimethyl-7-hydroxy-2-octen-1,6-olide and (E)-6,7-Dihydroxy-3,7-dimethyl-2-octenic Acid[J]. Chinese Journal of Organic Chemistry, 2014 , 34(11) : 2350 -2353 . DOI: 10.6023/cjoc201406005

References

[1] Gallardo, G. L.; Pena, N. I.; Cabrera, G. M. Phytochem. Lett. 2008, 1, 155.
[2] Yang, Y.; Jiang, J. Z.; Yan, X. J.; Zhao, J. X.; Yuan, H. Z.; Qin, Z. H.; Wang, M. A. Molecules 2010, 15, 7075.
[3] Lee, K. Y.; Kim, S. H.; Sung, S. H. Planta Med. 2008, 74, 867.
[4] Chen, J.; Zhu, C. L.; Xu, H. Y.; Ni, X.; Yang, P. M. Chin. J. Pharm. 2010, 41, 504 (in Chinese).(陈佳, 朱超兰, 许海燕, 倪翔, 杨培明, 中国医药工业杂志, 2010, 41, 504.)
[5] Burton, A. F.; McLean, D. US 5175190, 1992 [Chem. Abstr. 1993，118, 132158].
[6] Dong, H. B.; Yang, M. Y.; Jiang, J. Z.; Wang, M. A. J. Asian Nat. Prod. Res. 2013, 15, 880.
[7] Francois, P. T. Tetrahedron Lett. 2004, 45, 5519.
[8] Kaori, A. J. Org. Chem. 2000, 64, 4745.
[9] Da Silva, E. B. P.; Soares, M. G.; Mariane, B.; Vallim, M. A.; Pascon, R. C.; Sartorelli, P.; Lago, J. H. G. Molecules 2013, 18, 13574.
[10] Gonzalez, A. M.; Gonzalez, B. C.; Cancho, G. B.; Simal, G. J. Food Chem. 2012, 131, 826.
[11] Esumi, T.; Yamamoto, C.; Fukuyama, Y. Synlett 2013, 1845.
[12] Chatterjee, T. Biotechnol. Appl. Biochem. 2004, 39, 303.

Options
Outlines

/

〈 〉