Study on Synthesis of (S)-Methyl 2-(2, 2, 5, 5-Tetramethyl-1, 3-Dioxolan-4-Yl)Thiazole-4-Carboxylic Acid Methyl Ester

Article Preview

Abstract:

(S)-methyl 2-(2, 2, 5, 5-tetramethyl-1, 3-dioxolan-4-yl) thiazole-4-carboxylic acid methyl ester, the unit containing thiazole of a cyclic depsipeptide Lyngbyabellin A which exhibited moderate cytotoxicity against KB and LoVo cells, was synthesized from methyl 3, 3-dimethylacrylate in overall yield 13.8% through nine steps, including asymmetric dihydroxylation, 2, 2-dimethoxypropane protection, saponification, coupling reaction, sulphonation, diazotization, cyclization, oxidation, and so on.

You might also be interested in these eBooks

Info:

Periodical:

Advanced Materials Research (Volumes 781-784)

Pages:

1175-1179

Citation:

Online since:

September 2013

Export:

Price:

Permissions CCC:

Permissions PLS:

Сopyright:

© 2013 Trans Tech Publications Ltd. All Rights Reserved

Share:

Citation:

* - Corresponding Author

[1] Luesch, H.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J.; Mooberry, S. L. J. Nat. Prod. Vol. 63 (2000), p.611.

Google Scholar

[2] Shalaby, M.A.; Grote, C.W. ; Rapopport, H.J. Org. Chem. Vol. 61 (1996), p.9045.

Google Scholar

[3] Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa, K.; Wang, Z. M.; Xu, D.; Zhang, X. L. J. Org. Chem. Vol. 57 (1992).

DOI: 10.1021/jo00036a003

Google Scholar

[4] Wipf, P.; Fritch, P. C. Tetrahedron Lett. Vol. 35 (1994), p.5397.

Google Scholar

[5] Atkins, G. M.; Burgess, E. M. J. Am. Chem. Soc. Vol. 90 (1968), p.4744.

Google Scholar

[6] Boden, C. D.; Pattenden, G.; Ye, T. Synlett 1995, p.417.

Google Scholar