Contiguous stereogenic quaternary carbons: A daunting challenge in natural products synthesis

Proceedings of the National Academy of Sciences of the United States of America

Volumn 101, Issue 33, 2004, Pages 11943-11948

  Peterson, Emily A ^a   Overman, Larry E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

APHIDICOLIN; CARBON; CHIMONANTHINE; DAMMARANE DERIVATIVE; DAMMARANEDIOL; IDIOSPERMULINE; MARITIMOL; NATURAL PRODUCT; SECODAPHNIPHYLLINE; THIOLACTAM; TRICHODIENE; UNCLASSIFIED DRUG;

CHEMICAL MODIFICATION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; QUATERNARY; REVIEW; STEREOCHEMISTRY;

ALKALOIDS; BIOLOGICAL PRODUCTS; CARBON; CHEMISTRY, ORGANIC; CYCLOPARAFFINS; STEREOISOMERISM;

EID: 4344593453     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.0402416101     Document Type: Review

References (41)

1. Johnson, W. S. (1976) Angew. Chem. Int. Ed. Engl. 15, 9-17.
2. Stork, G. & Burgstahler, A. W. (1955) J. Am. Chem. Soc. 77, 5068-5077.
3. Eschenmoser, A., Ruzicka, L., Jeger, O. & Arigoni, D. (1955) Helv. Chim. Acta 38, 1890-1904.
4. Johnson, W. S., Lindell, S. D. & Steele, J. (1987) J. Am. Chem. Soc. 109, 5852-5853.
5. Corey, E. J. & Lin, S. (1996) J. Am. Chem. Soc. 118, 8765-8766.
6. Kolb, H. C., VanNieuwenhze, M. S. & Sharpless, K. B. (1994) Chem. Rev. 94, 2483-2547.
7. Corey, E. J., Noe, M. C. & Lin, S. (1995) Tetrahedron Lett. 36, 8741-8744.
8. Reich, H. J., Olson, R. E. & Clark, M. C. (1980) J. Am. Chem. Soc. 102, 1423-1424.
9. Heathcock, C. H. & Stafford, J. A. (1992) J. Org. Chem. 57, 2566-2574.
10. Heathcock, C. H., Hansen, M. M., Ruggeri, R. B. & Kath, J. C. (1992) J. Org. Chem. 57, 2544-2553.
11. Heathcock, C. H. (1996) Proc. Natl. Acad. Sci. USA 93, 14323-14327.
12. Stafford, J. A. & Heathcock, C. H. (1990) J. Org. Chem. 55, 5433-5434.
13. Toró, A., Nowak, P. & Deslongchamps, P. (2000) J. Am. Chem. Soc. 122, 4526-4527.
14. Hufford, C. D., Guerrero, R. O. & Doorenbos, N. J. (1976) J. Pharm. Sci. 95, 778-780.
15. Toyota, M. & Ihara, M. (1999) Tetrahedron 55, 5641-5679.
16. Corey, E. J. & Cheng, X.-M. (1995) The Logic of Chemical Synthesis (Wiley, New York).
17. Brillon, D. & Deslongchamps, P. (1986) Tetrahedron Lett. 27, 1131-1134.
18. Toró, A., Lemelin, C.-A., Préville, P., Bélanger, G. & Deslongchamps, P. (1999) Tetrahedron 55, 4655-4684.
19. Montforts, F.-P. & Schwartz, U. M. (1991) Liebigs Ann. Chem. 8, 709-725.
20. Enders, D., Fey, P. & Kipphardt, H. (1987) Org. Synth. 65, 173-182.
21. Piers, E., Abeysekera, B. F., Herbert, D. J. & Suckling, I. D. (1985) Can. J. Chem. 63, 3418-3432.
22. Durand-Reville, T., Gobbi, L. B., Gray, B. L., Ley, S. V. & Scott, J. S. (2002) Org. Lett. 4, 3847-3850.
23. Lemieux, R. M. & Meyers, A. I. (1998) J. Am. Chem. Soc. 120, 5453-5457.
24. Pearson, A. J. & O'Brien, M. K. (1989) J. Org. Chem. 54, 4663-4673.
25. Romo, D. & Meyers, A. I. (1991) Tetrahedron 47, 9503-9569.
26. Devine, P. N. & Meyers, A. I. (1994) J. Am. Chem. Soc. 116, 2633-2634.
27. Beslin, P., Lagain, D. & Vialle, J. (1980) J. Org. Chem. 45, 2517-2518.
28. Holton, R. A., Kennedy, R. M., Kim, H.-B. & Krafft, M. E. (1987) J. Am. Chem. Soc. 109, 1597-1600.
29. Brundret, K. M., Dalziel, W., Hesp, B., Jarvis, J. A. J. & Neidle, S. (1972) J. Chem. Soc. Chem. Commun. 18, 1027-1028.
30. Corey, E. J., Tius, M. A. & Das, J. (1980) J. Am. Chem. Soc. 102, 1742-1744.
31. Holton, R. A., Williams, A. D. & Kennedy, R. M. (1986) J. Org. Chem. 51, 5480-5482.
32. Holton, R. A. & Kim, H.-B. (1986) Tetrahedron Lett. 27, 2191-2194.
33. Overman, L. E. & Peterson, E. A. (2003) Angew. Chem. Int. Ed. Engl. 42, 2525-2528.
34. Overman, L. E., Larrow, J. F., Stearns, B. A. & Vance, J. M. (2000) Angew. Chem. Int. Ed. Engl. 39, 213-215.
35. Lebsack, A. D., Link, J. T., Overman, L. E. & Stearns, B. A. (2002) J. Am. Chem. Soc. 124, 9008-9009.
36. Overman, L. E. & Peterson, E. A. (2003) Tetrahedron 59, 6905-6919.
37. Hoyt, S. B. & Overman, L. E. (2000) Org. Lett. 2, 3241-3244.
38. Dounay, A. B. & Overman, L. E. (2003) Chem. Rev. 103, 2945-2964.
39. Overman, L. E., Paone, D. V. & Stearns, B. A. (1999) J. Am. Chem. Soc. 121, 7702-7703.
40. Douglas, C. J. & Overman, L. E. (2004) Proc. Natl. Acad. Sci. USA 101, 5363-5367.
41. Helmchen, G., Hoffmann, R. W., Mulzer, J. & Schaumann, E., eds. (1996) in Methods of Organic Chemistry (Houben-Weyl, Workbook Edition) (Thieme, Stuttgart), 4th Ed., Vol. E21/2, pp. 1077-1118.