Progress toward the total synthesis of guanacastepene A

Synlett

Volumn , Issue 11, 2006, Pages 1623-1644

  Maifeld, Sarah V ^a   Lee, Daesung ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Diterpene; Guanacastepene; Total synthesis

Indexed keywords

ALDEHYDE DERIVATIVE; AZULENE DERIVATIVE; CARBON; DITERPENE; GUANACASTEPENE A; KETENE DERIVATIVE; METHYL GROUP; NATURAL PRODUCT; OXYGEN; UNCLASSIFIED DRUG;

ALDOL REACTION; ANTIMICROBIAL ACTIVITY; DIELS ALDER REACTION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGUS; HUMAN; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; REVIEW;

EID: 33746282468     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-944213     Document Type: Review

References (62)

1. Brady, S. F.; Singh, M. P.; Janso, J. E.; Clardy, J. J. Am. Chem. Soc. 2000, 122, 2116.
2. Henkel, T.; Brunne, R. M.; Müller, H.; Reichel, F. Angew. Chem. Int. Ed. 1999, 38, 643.
3. Singh, M. P.; Janso, J. E.; Luckman, S. W.; Brady, S. F.; Clardy, J.; Greenstein, M.; Maiese, W. M. J. Antibiot. 2000, 53, 256.
4. Tan, D. S.; Dudley, G. B.; Danishefsky, S. J. Angew. Chem. Int. Ed. 2002, 41, 2185.
5. Brady, S. F.; Bondi, S. M.; Clardy, J. J. Am. Chem. Soc. 2001, 123, 9900.
6. Mischne, M. Curr. Org. Synth. 2005, 2, 261.
7. (a) Mandal, M.; Yun, H.; Dudley, G. B.; Lin, S.; Tan, D. S.; Danishefsky, S. J. J. Org. Chem. 2005, 70, 10619.
8. (b) Yun, H.; Danishefsky, S. J. Tetrahedron Lett. 2005, 46, 3879.
9. (c) Mandal, M.; Danishefsky, S. J. Tetrahedron Lett. 2004, 45, 3831.
10. (d) Mandal, M.; Danishefsky, S. J. Tetrahedron Lett. 2004, 45, 3827.
11. (e) Dudley, G. B.; Danishefsky, S. J.; Sukenick, G. Tetrahedron Lett. 2002, 43, 5605.
12. (f) Lin, S.; Dudley, G. B.; Tan, D. S.; Danishefsky, S. J. Angew. Chem. Int. Ed. 2002, 41, 2188.
13. (g) Tan, D. S.; Dudley, G. B.; Danishefsky, S. J. Angew. Chem. Int. Ed. 2002, 41, 2185.
14. (h) Dudley, G. B.; Tan, D. S.; Kim, G.; Tanski, J. M.; Danishefsky, S. J. Tetrahedron Lett. 2001, 42, 6789.
15. Dudley, G. B.; Danishefsky, S. J. Org. Lett. 2001, 3, 2399.
16. (a) Shi, B.; Hawryluk, N. A.; Snider, B. B. J. Org. Chem. 2003, 68, 1030.
17. (b) Snider, B. B.; Shi, B. Tetrahedron Lett. 2001, 42, 9123.
18. (c) Snider, B. B.; Hawryluk, N. A. Org. Lett. 2001, 3, 569.
19. (a) Boyer, F.-D.; Hanna, I.; Ricard, L. Org. Lett. 2004, 6, 1817.
20. (b) Boyer, F.-D.; Hanna, I. Tetrahedron Lett. 2002, 43, 7469.
21. (a) Mehta, G.; Pallavi, K.; Umarye, J. D. Chem. Commun. 2005, 4456.
22. (b) Mehta, G.; Umarye, J. D.; Srinivas, K. Tetrahedron Lett. 2003, 44, 4233.
23. (c) Mehta, G.; Umarye, J. D.; Srinivas, K. Tetrahedron Lett. 2002, 43, 6975.
24. (d) Mehta, G.; Umarye, J. D. Org. Lett. 2002, 4, 1063.
25. (a) Magnus, P.; Ollivier, C. Tetrahedron Lett. 2002, 43, 9605.
26. (b) Magnus, P.; Waring, M. J.; Ollivier, C.; Lynch, V. Tetrahedron Lett. 2001, 42, 4947.
27. (a) Evans, D. A.; Andrews, G. C. Acc. Chem. Res. 1974, 7, 147.
28. (b) Zhou, Z. S.; Flohr, A.; Hilvert, D. J. Org. Chem. 1999, 64, 8334.
29. Nakazaki, A.; Sharma, U.; Tius, M. A. Org. Lett. 2002, 4, 3363.
30. Chiu, P.; Li, S. Org. Lett. 2004, 6, 613.
31. Srikrishna, A.; Dethe, D. H. Org. Lett. 2004, 6, 165.
32. Quinkert, G.; Müller, T.; Königer, A.; Schultheis, O.; Sickenberger, B.; Dürner, G. Tetrahedron Lett. 1992, 33, 3469.
33. Shipe, W. D.; Sorensen, E. J. Org. Lett. 2002, 4, 2063.
34. (a) Hughes, C. C.; Miller, A. K.; Trauner, D. Org. Lett. 2005, 7, 3425.
35. (b) Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113.
36. Wright, D. L.; Whitehead, C. R.; Sessions, E. H.; Ghiviriga, I.; Frey, D. A. J. Am. Chem. Soc. 1999, 121, 1535.
37. Mihelcic, J.; Moeller, K. D. J. Am. Chem. Soc. 2004, 126, 9106.
38. (a) Du, X.; Chu, H. V.; Kwon, O. Tetrahedron Lett. 2004, 45, 8843.
39. (b) Du, X.; Chu, H. V.; Kwon, O. Org. Lett. 2003, 5, 1923.
40. Li, C.-C.; Liang, S.; Zhang, X.-H.; Xie, Z.-X.; Chen, J.-H.; Wu, Y.-D.; Yang, Z. Org. Lett. 2005, 7, 3709.
41. Brummond, K. M.; Gao, D. Org. Lett. 2003, 5, 3491.
42. (a) Nguyen, T. M.; Seifert, R. J.; Mowrey, D. R.; Lee, D. Org. Lett. 2002, 4, 3959.
43. (b) Nguyen, T. M.; Lee, D. Tetrahedron Lett. 2002, 43, 4033.
44. Meyers, A. G.; Hammond, M.; Wu, Y.; Xiang, J.-N.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1996, 118, 10006.
45. Burke, S. D.; Buchanan, J. L.; Rovin, J. D. Tetrahedron Lett. 1991, 32, 3961.
46. Sivik, M. R.; Stanton, K. J.; Paquette, L. A. Org. Synth. 1995, 72, 57.
47. (a) Erman, W. F. J. Am. Chem. Soc. 1967, 89, 3828.
48. (b) Erman, W. F. J. Am. Chem. Soc. 1967, 89, 779.
49. A slight loss of optical purity (13%) was noted in the photorearrangement, presumably due to a process involving fragmentation of the diradical to an intermediate ketene.
50. (a) Kulkarni, Y. S.; Niwa, M.; Ron, E.; Snider, B. B. J. Org. Chem. 1987, 52, 1568.
51. (b) Erman, W. F.; Wenkert, E.; Jeffs, P. W. J. Org. Chem. 1968, 34, 2196.
52. Murthy, A. R.; Sundar, N. S.; Rao, G. S. R. S. Tetrahedron 1982, 58, 2831.
53. (a) Black, T. H. Aldrichimica Acta 1983, 16, 3.
54. (b) Cushman, M.; Cheng, L. J. Org. Chem. 1978, 43, 286.
55. Hareau, G. P.-J.; Koiwa, M.; Hikichi, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3640; and references cited therein.
56. Lipshutz, B. H.; Wood, R. H.; Tirado, R. Org. Synth. 1999, 76, 252.
57. (a) Zakarian, A.; Batch, A.; Holton, R. A. J. Am. Chem. Soc. 2003, 125, 7822.
58. (b) Zhu, L.; Weymeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445.
59. (a) Kim, M.; Park, S.; Maifeld, S. V.; Lee, D. J. Am. Chem. Soc. 2004, 126, 10242.
60. (b) Hansen, E.; Lee, D. J. Am. Chem. Soc. 2004, 126, 15074.
61. (c) Maifeld, S. V.; Miller, R. L. J. Am. Chem. Soc. 2004, 126, 12228.
62. (d) Miller, R. L.; Maifeld, S. V.; Lee, D. Org. Lett. 2004, 6, 2773.