Skip to content
Publicly Available Published by De Gruyter January 1, 2009

Synthesis of an analog of mycothiazole and total synthesis of pseudotrienic acid B

  • Dominique Amans , Alexandre Le Flohic , Véronique Bellosta , Christophe Meyer and Janine Cossy

Abstract

An analog of mycothiazole and pseudotrienic acid B were synthesized efficiently by using ring-closing metathesis or cross-metathesis as key reactions.


Conference

International Symposium on Chemistry of Natural Products (ISCNP-25) and 5th International Conference on Biodiversity (ICOB-5), International Conference on Biodiversity, International Symposium on the Chemistry of Natural Products, ICOB, ISCNP, Biodiversity, Natural Products, 25th, Kyoto, Japan, 2006-07-23–2006-07-28


References

1. doi:10.1021/ja00221a042, P. Crews, Y. Kakou, E. Quinoa. J. Am. Chem. Soc. 110, 4365 (1988).Search in Google Scholar

2. doi:10.1002/1099-0690(200102)2001:4<775::AID-EJOC775>3.0.CO;2-Z, A. Cutignano, I. Bruno, G. Bifulco, A. Casapullo, C. Debitus, L. Gomez-Paloma, R. Riccio. Eur. J. Org. Chem. 775 (2001).Search in Google Scholar

3. The results of the National Cancer Institute Human Tumor Cell Line Screen mean graph can be consulted on the Internet at <http://www.dtp.nci.nih.gov> (NCS number 647640).Search in Google Scholar

4. doi:10.1021/np0503597, R. N. Sonnenschein, T. A. Johnson, K. Tenney, F. A. Valeriote, P. Crews. J. Nat. Prod. 69, 145 (2006).Search in Google Scholar

5. (a) doi:10.1021/ol000128l, H. Sugiyama, F. Yokokawa, T. Shioiri. Org. Lett. 2, 2149 (2000);Search in Google Scholar

5. (b) doi:10.1016/S0040-4020(03)01020-2, H. Sugiyama, F.Yokokawa, T. Shioiri. Tetrahedron 59, 6579 (2003).Search in Google Scholar

6. doi:10.1021/ol990909q, M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs. Org. Lett. 1, 953 (1999).Search in Google Scholar

7. S. Karsch, P. Schwab, P. Metz. Synlett 2019 (2002).Search in Google Scholar

8. A. Le Flohic, C. Meyer, J. Cossy, J.-C. Galland, J.-R. Desmurs. Synlett 667 (2003).Search in Google Scholar

9. doi:10.1021/ol047603q, A. Le Flohic, C. Meyer, J. Cossy. Org. Lett. 7, 339 (2005).Search in Google Scholar

10. doi:10.1016/j.tet.2006.07.010, A. Le Flohic, C. Meyer, J. Cossy. Tetrahedron 62, 9017 (2006).Search in Google Scholar

11. (a) doi:10.1016/S0040-4039(98)01743-2, B. Plietker, P. Metz. Tetrahedron Lett. 39, 7827 (1998);Search in Google Scholar

11. (b) doi:10.1002/1099-0690(200110)2001:19<3669::AID-EJOC3669>3.0.CO;2-S, B. Plietker, D. Seng, R. Frohlich, P. Metz. Eur. J. Org. Chem. 3669 (2001).Search in Google Scholar

12. doi:10.1021/np050243a, A. Pohanka, A. Broberg, M. Johansson, L. Kenne, J. Levenfors. J. Nat. Prod. 68, 1380 (2005).Search in Google Scholar

13. doi:10.1021/ja983222u, J. S. Kingsbury, J. P. A. Harrity, P. J. Bonitatebus Jr., A. H. Hoveyda. J. Am. Chem. Soc. 121, 791 (1999).Search in Google Scholar

14. doi:10.1021/ja00033a005, A. Hafner, R. O. Duthaler, R. Marti, J. Rihs, P. Rhote-Streit, F. Schwarzenbach. J. Am. Chem. Soc. 114, 2321 (1992).Search in Google Scholar

15. The 2R,3R absolute configuration of 13 was confirmed by the 1H NMR spectra of the two corresponding mandelates, according to the procedure described in J. M. Seco, E. Quinoa, R. Riguera. Tetrahedron: Asymmetry 12, 2915 (2001).10.1016/S0957-4166(01)00508-0Search in Google Scholar

16. doi:10.1021/jo00332a045, P. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless. J. Org. Chem. 46, 3936 (1981).Search in Google Scholar

17. doi:10.1016/S0040-4039(01)93712-8, B. H. Lipshutz, E. L. Ellworth, S. H. Dimock, D. C. Reuter. Tetrahedron Lett. 30, 2065 (1989).Search in Google Scholar

18. doi:10.1002/anie.200601114, D. Amans, V. Bellosta, J. Cossy. Angew. Chem., Int. Ed. 45, 5870 (2006).Search in Google Scholar

Published Online: 2009-01-01
Published in Print: 2007-01-01

© 2013 Walter de Gruyter GmbH, Berlin/Boston

Downloaded on 20.4.2024 from https://www.degruyter.com/document/doi/10.1351/pac200779040677/html
Scroll to top button