Asymmetric synthesis of salvinorin A, a potent κ opioid receptor agonist

Journal of the American Chemical Society

Volumn 129, Issue 29, 2007, Pages 8968-8969

  Scheerer, Jonathan R ^a   Lawrence, Jonathan F ^a   Wang, Grace C ^a   Evans, David A ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KAPPA OPIATE RECEPTOR AGONIST; SALVINORIN A;

ARTICLE; ASYMMETRIC SYNTHESIS; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

ALDEHYDES; CATALYSIS; CYCLIZATION; DITERPENES; INDICATORS AND REAGENTS; KINETICS; PALLADIUM; RECEPTORS, OPIOID, KAPPA;

EID: 34547479422     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja073590a     Document Type: Article

References (30)

1. Ortega, A.; Blount, J. F.; Manchand, P. S. J. Chem. Soc., Perkin Trans. I 1982, 10, 2505-2508.
2. (a) Roth, B. L.; Baner, K.; Westkaemper, R.; Siebert, D.; Rice, K. C.; Steinberg, S.; Ernsberger, P.; Rothman, R. B. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 11934-11939.
3. (b) For molecular mechanism studies of KOR binding, see: Yan, F.; Mosier, P. D.; Westkaemper, R. B.; Stewart, J.; Zjawiony, J. K.; Vortherms, T. A.; Sheffler, D. J.; Roth, B. L. Biochemistry 2005, 44, 8643-8651.
4. Shirota, O.; Nagamatsu, K.; Sekita, S. J. Nat. Prod. 2006, 69, 1782-1786 and references therein.
5. (a) Beguin, C.; Richards, M. R.; Li, J.; Wang, Y.; Xu, W.; Liu-Chen, L.; Carlezon, W. A., Jr.; Cohen, B. M. Bioorg. Med. Chem. Lett. 2006, 16, 4679-4685 and references therein.
6. (b) Tidgewell, K.; Harding, W. W.; Lozama, A.; Cobb, H.; Shah, K.; Kannan, P.; Dersch, C. M.; Parrish, D.; Deschamps, J. R.; Rothman, R. B.; Prisinzano, T. E. J. Nat. Prod. 2006, 69, 914-918 and references therein.
7. (a) Evans, D. A.; Starr, J. T. Angew. Chem., Int. Ed. 2002, 41, 1787-1790.
8. (b) Evans, D. A.; Scheerer, J. R. Angew. Chem., Int. Ed. 2005, 44, 6038-6042.
9. Ho, T. Tandem Organic Reactions; Wiley & Sons: New York, 1992; Chapter 3, pp 33-56.
10. Still, W. C.; Galynker, I. Tetrahedron 1981, 37, 3981-3996.
11. Evans, D. A.; Thomson, R. J. J. Am. Chem. Soc. 2005, 128, 10506-10507.
12. Pollet, P.; Gelin, S. Synthesis 1978, 142-143.
13. Cahiez, G.; Avedissian, H. Synthesis 1998, 1199-1205.
14. Nagao, Y.; Fujita, E. J. Org. Chem. 1986, 51, 2391-2393.
15. 7-diastereomer because molecular modeling studies suggested a gearing effect, potentially rendering the macrolactonization of 16 more facile.
16. Frantz, D. E.; Fassler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806-1807.
17. 2- diastereomer with NaH cleanly afforded benzyloxymethylated product.
18. Dupau, P.; Epple, R.; Thomas, A. A.; Fokin, V. V.; Sharpless, K. B. Adv. Synth. Catal. 2002, 344, 421-433.
19. Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012 and references therein.
20. Brown, C. A.; Yamashita, A. J. Am. Chem. Soc. 1975, 97, 891-893.
21. Negishi, E.; Van Horn, D. E.; King, A. O.; Okukado, N. Synthesis 1979, 79, 501-502.
22. (a) Shiina, I.; Kubota, M.; Ibuka, R.; Tetrahedron Lett. 2002, 43, 7535-7539.
23. (b) Shiina, I.; Kubota, M.; Oshiumi, H.; Hashizume, M. J. Org. Chem. 2004, 69, 1822-1830.
24. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299-6302.
25. Kotsuki, H.; Datta, P. K.; Hayakawa, H.; Suenaga, H. Synthesis 1995, 1348-1350.
26. (a) Ganem, B.; Fortunato, J. M. J. Org. Chem. 1975, 40, 2846-2848.
27. (b) Fortunato, J. M.; Ganem, B. J. Org. Chem. 1976, 41, 2194-2200.
28. This likely is due to the small energy difference between chair and boat δ-lactones. See: (a) Thomas, S. A. J. Crystallogr. Spectrosc. Res. 1985, 15, 115-131.
29. (b) Stanley, J.; Matallana, A.; Kinsbury, C. A. J. Phy. Org. Chem. 1990, 3, 419-427.
30. For a review of TADA reactions in synthesis, see: Marsault, E.; Toro, A.; Nowak, P.; Deslongchamps, P. Tetrahedron 2001, 57, 4243-4260.