Revised structure of deacetyl-1,10-didehydrosalvinorin G

Tetrahedron Letters

Volumn 48, Issue 31, 2007, Pages 5461-5464

  Ma, Zhongze ^a   Lee, David Y W ^a  

^a MCLEAN HOSPITAL   (United States)

Author keywords

Epimer; NMR; Revised structure; Salvinorin A

Indexed keywords

DEACETYL 1,10 DIDEHYDROSALVINORIN G; SALVINORIN A; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 34347336419     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.05.179     Document Type: Article

References (25)

1. Ortega A., Blount J.F., and Manchand P.S. J. Chem. Soc., Perkin Trans. 1 (1982) 2505-2508
2. Valdes III L.J., Butler W.M., Hatfield G.M., Paul A.G., and Koreeda M. J. Org. Chem. 49 (1984) 4716-4720
3. Roth B.L., Baner K., Westkaemper R., Siebert D.J., Rice K.C., Steinberg S., Ernsberger P., and Rothman R.B. Proc. Natl. Acad. Sci. 99 (2002) 11934-11939
4. Sheffler D.J., and Roth B.L. Trends Pharmacol. Sci. 24 (2003) 107-109
5. Siebert D.J. J. Ethnopharmacol. 43 (1994) 53-56
6. Chavkin C., Sub S., Jin W., Stewart J., Zjawiony J.K., Siebert D.J., Toth B.A., Hufeisen S.J., and Roth B.L. J. Pharmacol. Exp. Ther. 308 (2004) 1197-1203
7. Beguin C., Richards M.R., Wang Y., Chen Y., Liu-Chen L.-Y., Ma Z., Lee D.Y.W., Carlezon W.A., and Cohen B.M. Bioorg. Med. Chem. Lett. 15 (2005) 2761-2765
8. Lee D.Y.W., Karnati V.V.R., He M., Liu-Chen L.-Y., Kondaveti L., Ma Z., Wang Y., Chen Y., Beguin C., Carlezon W.A., and Cohen B. Bioorg. Med. Chem. Lett. 15 (2005) 3744-3747
9. Lee D.Y.W., Ma Z., Liu-Chen L.-Y., Wang Y., Chen Y., Carlezon W.A., and Cohen B. Bioorg. Med. Chem. 13 (2005) 5635-5639
10. Munro T.A., Rizzacasa M.A., Roth B.L., Toth B.A., and Yan F. J. Med. Chem. 48 (2005) 345-348
11. Lee D.Y.W., He M., Kondaveti L., Liu-Chen L.-Y., Ma Z., Wang Y., Chen Y., Li J.-G., Beguin C., Carlezon W.A., and Cohen B. Bioorg. Med. Chem. Lett. 15 (2005) 4169-4173
12. Harding W.W., Tidgewell K., Byrd N., Cobb H., Dersch C.M., Butelman E.R., Rothman R.B., and Prisinzano T.E. J. Med. Chem. 48 (2005) 4765-4771
13. Munro T.A., Goetchius G.W., Roth B.L., Vortherms T.A., and Rizzacasa M.A. J. Org. Chem. 70 (2005) 10057-10061
14. Harding W.W., Schmidt M., Tidgewell K., Kannan P., Holden K.G., Dersch C.M., Rothman R.B., and Prisinzano T.E. Bioorg. Med. Chem. Lett. 16 (2006) 3170-3174
15. Beguin C., Richards M.R., Li J.-G., Wang Y., Xu W., Liu-Chen L.-Y., Carlezon W.A., and Cohen B.M. Bioorg. Med. Chem. Lett. 16 (2006) 4679-4685
16. Lee D.Y.W., He M., Liu-Chen L.-Y., Wang Y., Li J.-G., Xu W., Ma Z., Carlezon W.A., and Cohen B. Bioorg. Med. Chem. Lett. 16 (2006) 5498-5502
17. Tidgewell K., Harding W.W., Lozama A., Cobb H., Shah K., Kannan P., Dersch C.M., Parrish D., Deschamps J.R., Rothman R.B., and Prisinzano T.E. J. Natl. Prod. 69 (2006) 914-918
18. Bikbulatov R.V., Yan F., Roth B.L., and Zjawiony J.K. Bioorg. Med. Chem. Lett. 17 (2007) 2229-2232
19. Valdes III L.J., Chang H.-M., Visger D.C., and Koreeda M. Org. Lett. 3 (2001) 3935-3937
20. Munro, T. A. The Chemistry of Salvia divinorum. Ph.D. Thesis, University of Melbourne, Victoria, Australia, 2006; pp 92, 121, 188, 224. [http://eprints.infodiv.unimelb.edu.au/archive/00002327].
21. Munro, T. A.; Duncan, K. K.; Staples, R. J.; Xu, W.; Liu-Chen, L.-Y.; Beguin, C.; Carlezon, W. A.; Cohen, B. M. Beilstein J. Org. Chem. 2007, 3. [http://bjoc.beilstein-journals.org/content/pdf/1860-5397-3-1.pdf].
22. Ma Z.Z., Hano Y., Qiu F., Chen Y.J., and Nomura T. Tetrahedron Lett. 45 (2004) 3261-3263
23. Giner J.L., Kiemle D.J., Kutrzeba L., and Zjawiony J. Magn. Reson. Chem. 45 (2007) 351-354
24. +).
25. Munro T.A., and Rizzacasa M.A. J. Natl. Prod. 66 (2003) 703-705