Asymmetric total synthesis of (-)-plicatic acid via a highly enantioselective and diastereoselective nucleophilic epoxidation of acyclic trisubstitued olefins

Journal of the American Chemical Society

Volumn 131, Issue 30, 2009, Pages 10384-10385

  Sun, Bing Feng ^a   Hong, Ran ^a   Kang, Yan Biao ^a   Deng, Li ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; ASYMMETRIC EPOXIDATION; ASYMMETRIC TOTAL SYNTHESIS; CHEMICAL EQUATIONS; DIASTEREOSELECTIVE; DIASTEREOSELECTIVE EPOXIDATION; ENANTIOSELECTIVE; NEW STRATEGY; NUCLEOPHILIC EPOXIDATION; PLICATIC ACID; RING OPENING; STEREOSELECTIVE CONSTRUCTION; TERTIARY STEREOCENTERS; TOTAL SYNTHESIS;

ACIDS; FRIEDEL-CRAFTS REACTION; OLEFINS; STEREOSELECTIVITY; STRATEGIC PLANNING;

SYNTHESIS (CHEMICAL);

ACRYLIC ACID DERIVATIVE; ALKENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; EPOXIDE; HYDROPEROXIDE DERIVATIVE; LIGNAN DERIVATIVE; NUCLEOPHILE; PLICATIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; EPOXIDATION; FRIEDEL CRAFTS REACTION; RING OPENING; STEREOCHEMISTRY; SUBSTITUTION REACTION;

ALKENES; EPOXY COMPOUNDS; LIGNANS; NAPHTHOLS; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 68049088919     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9039407     Document Type: Article

References (40)

1. (a) Chan-Yeung, M.; Giclas, P. C.; Henson, P. M. J. Aller. Clin. Immun. 1980, 65, 333.
2. (b) Cartier, A.; Chan, H.; Malo, J.-L.; Pineau, L.; Tse, K. S.; Chan-Yeung, M. J. Allergy Clin. Immunol. 1986, 77, 639.
3. (c) Frew, A.; Chang, J. H.; Chan, H.; Quirce, S.; Noertjojo, K.; Keown, P.; Chan-Yeung, M. J. Allergy Clin. Immunol. 1998, 101, 841.
4. (d) Weissman, D. N.; Lewis, D. M. Occup. Med. 2000, 15, 385.
5. (e) Chan-Yeung, M. J. Allergy Clin. Immunol. 1982, 70, 32.
6. (f) Vedal, S.; Chan-Yeung, M.; Enarson, D. A.; Chan, H.; Dorken, E.; Tse, K. S. J. Allergy Clin. Immunol. 1986, 78, 1103.
7. (g) Chan-Yeung, M.; Chan, H.; Tse, K. S.; Salari, H.; Lam, S. J. Allergy Clin. Immunol. 1989, 85, 762.
8. (a) Gradner, J. A. F.; Barton, G. M.; MacLean, H. Can. J. Chem. 1959, 37, 1703.
9. (b) Gradner, J. A. F.; Swan, E. P.; Sutherland, S. A.; MacLean, H. Can. J. Chem. 1966, 44, 52.
10. (c) Swan, R. J.; Klyne, W.; MacLean, H. Can. J. Chem. 1967, 45, 321.
11. For a survey of chiroptical studies on tetralinlignans, see: Hulbert, P. B.; Klyne, W.; Scopes, P. M. J. Chem. Res. (S) 1981, 27.
12. For selectedrecent lignans syntheses, see: (a) Sefkow, M. Top. Curr. Chem. 2005, 243, 185.
13. (b) Wu, Y.; Zhao, J.; Chen, J.; Pan, C.; Li, L.; Zhang, H. Org. Lett. 2009, 11, 597.
14. (c) Kiran, M.; Subrata, G. Tetrahedron Lett. 2008, 49, 3433.
15. (d) Fukuyama, Y.; Harada, K.; Esumi, T.; Hojyo, D.; Kujime, Y.; Kubo, N.; Kubo, M.; Hioki, H. Heterocycles 2008, 76, 551.
16. (e) Angle, S. R.; Choi, I.; Tham, F. S. J. Org. Chem. 2008, 73, 6268.
17. (f) Mitra, S.; Gurrala, S. R.; Coleman, R. S. J. Org. Chem. 2007, 72, 8724.
18. (g) Coleman, R. S.; Gurrala, S. R. Org. Lett. 2005, 7, 1849.
19. For examplesand reviews of asymmetric epoxidations of electron-deficient olefins,see: (a) Wang, X.; Reisinger, C. M.; List, B. J. Am. Chem. Soc. 2008, 130, 6070.
20. (b) Wang, B.; Wu, X. Y.; Wong, O. A.; Nettles, B.; Zhao, M.-X.; Chen, D.; Shi, Y. J. Org. Chem. 2009, 74, 3986.
21. (c) Lu, X.; Liu, Y.; Sun, B.; Cindric, B.; Deng, L. J. Am. Chem. Soc. 2008, 130, 8134.
22. (d) Reisinger, C. M.; Wang, X.; List, B. Angew. Chem., Int. Ed. 2008, 47, 8112.
23. (e) Shi, Y. Acc. Chem. Res. 2004, 37, 488.
24. For a recently reported stereospecific,base-catalyzed epoxidation, see: (f) Švenda, J.; Myers, A. G. Org. Lett. 2009, 11, 2437.
25. Aoki, M.; Seebach, D. Helv. Chim. Acta 2001, 84, 187.
26. Holmquist, C. R.; Roskamp, E. J. J. Org. Chem. 1989, 54, 3258.
27. (a) Bull, J. R.; Sickle, E. S. J. Chem. Soc., Perkin Trans. 1 2000, 4476.
28. (b) Pettus, T. R. R.; Wang, J. Tetrahedron Lett. 2004, 45, 5895.
29. (c) Imamoto, T.; Sugiura, Y. J. Organomet. Chem. 1985, 285, 4233.
30. (d) McAuliffe, J. C.; Stick, R. V. Aust. J. Chem. 1997, 50, 193.
31. For Lewis acid promoted nucleophilic addition toketones with lithium or magnesium reagents, see: (e) Aubrecht, K. B.; Winemiller, M. D.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 11084, and references therein.
32. (a) Park, H. S.; Lee, I. S.; Kwon, D. W.; Kim, Y. H. Chem. Commun. 1998, 2745.
33. (b) Miller, R. S.; Sealy, J. M.; Shabangi, M.; Kuhlman, M. L.; Fuchs, J. R.; Flowers, R. A., II. J. Am. Chem. Soc 2000, 122, 7718.
34. (a) Machrouhi, F.; Hamann, B.; Namy, J. L.; Kagan, H. Synlett 1996, 7, 633.
35. (b) Miquel, N.; Doisneau, G.; Beau, J.-M. Angew. Chem., Int. Ed. 2000, 39, 4111.
36. (a) Tamao, K.; Ishida, N.; Tanak, T.; Kumada, M. Organometallics 1983, 2, 1694.
37. (b) Tamao, K.; Ishida, N.; Kumada, M. J. Org. Chem. 1983, 48, 2122.
38. (a) Vaughan, W. R.; Baumann, J. B. J. Org. Chem. 1962, 27, 739.
39. (b) Lal, K.; Ghosh, S.; Salomon, R. G. J. Org. Chem. 1987, 52, 1072.
40. See the Supporting Information for details.