Tremorgenic indole alkaloids. The total synthesis of (-)-penitrem D

Journal of the American Chemical Society

Volumn 125, Issue 27, 2003, Pages 8228-8237

  Smith III, Amos B ^a   Kanoh, Naoki ^a   Ishiyama, Haruaki ^a   Minakawa, Noriaki ^a   Rainier, Jon D ^a   Hartz, Richard A ^a   Cho, Young Shin ^a   Cui, Haifeng ^a   Moser, William H ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOIDS;

OXIDATION; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

HYDROXYL GROUP; INDOLE ALKALOID; PENITREM D; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; AUTOOXIDATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TERTIARY; THERMOGENESIS;

INDOLE ALKALOIDS; MYCOTOXINS; PENICILLIUM;

EID: 0038682516     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034842k     Document Type: Article

References (70)

1. (a) Cole, R. J.; Dorner, J. W.; Lansden, J. A.; Cox, R. H.; Pape, C.; Cunfer, B.; Nicholson, S. S.; Bedell, D. M. J. Agric. Food Chem. 1977, 25, 1197-1201.
2. (b) Mantle, P. G.; Mortimer, P. H.; White, E. P. Res. Vet. Sci. 1978, 24, 49-56.
3. (c) di Menna, M. E.; Mantle, P. G. Res. Vet. Sci. 1978, 24, 347-351.
4. (d) Mantle, P. G.; Day, J. B.; Haigh, C. R.; Penny, R. H. Vet. Rec. 1978, 103, 403.
5. (e) Springer, J. P.; Clardy, J. Tetrahedron Lett. 1980, 21, 231-234.
6. (f) Gallagher, R. T.; Clardy, J.; Wilson, B. J. Tetrahedron Lett. 1980, 21, 239-242.
7. (g) Dorner, J. W.; Cole, R. J.; Cox, R. H.; Cunfer, B. M. J. Agric. Food Chem. 1984, 32, 1069-1071.
8. Brimblecombe, R. W.; Pinder, R. M. Tremorgens and Tremorgenic Agents; Scientechnia; Bristol, U.K., 1972; pp 14-15.
9. (a) Acklin, W.; Weibel, F.; Arigoni, D. Chimia 1977, 31, 63.
10. (b) de Jesus, A. E.; Hull, W. E.; Steyn, P. S.; van Heerden, F. R.; Vleggaar, R.; Wessels, P. L. J. Chem. Soc., Chem. Commun. 1982, 837-838.
11. (c) de Jesus, A. E.; Gorst-Allman, C. P.; Steyn, P. S.; van Heerden, F. R.; Vleggaar, R.; Wessels, P. L.; Hull, W. E. J. Chem. Soc., Perkin Trans. 1 1983, 1863-1868.
12. (a) Wilson, B. J.; Wilson, C. H.; Hayes, A. W. Nature 1968, 220, 77-78.
13. (b) de Jesus, A. E.; Steyn, P. S.; van Heerden, F. R.; Vleggaar, R.; Wessels, P. L.; Hull, W. E. J. Chem. Soc., Chem. Commun. 1981, 289-291.
14. (c) de Jesus, A. E.; Steyn, P. S.; van Heerden, F. R.; Vleggaar, R.; Wessels, P. L.; Hull, W. E. J. Chem. Soc., Perkin Trans. 1 1983, 1847-1856.
15. (a) Horeau, A. Tetrahedron Lett. 1961, 506-512.
16. (b) Horeau, A.; Sutherland, J. K. J. Chem. Soc., Org. 1966, 247-248.
17. (c) Herz, W.; Kagan, H. B. J. Org. Chem. 1967, 32, 216-218.
18. (a) Smith, A. B., III; Mewshaw, R. J. Am. Chem. Soc. 1985, 107, 1769-1771.
19. (b) Mewshaw, R. E.; Taylor, M. D.; Smith, A. B., III. J. Org. Chem. 1989, 54, 3449-3462.
20. (c) Smith, A. B., III; Sunazuka, T.; Leenay, T. L.; Kingery-Wood, J. J. Am. Chem. Soc. 1990, 112, 8197-8198.
21. (d) Smith, A. B., III; Kingery-Wood, J.; Leenay, T. L.; Nolen, E. G.; Sunazuka, T. J. Am. Chem. Soc. 1992, 114, 1438-1449.
22. (e) Smith, A. B., III; Cui, H. Org. Lett. 2003, 5, 587-590.
23. (f) Smith, A. B., III; Visnick, M. Tetrahedron Lett. 1985, 26, 3757-3760.
24. (g) Smith, A. B., III; Visnick, M.; Haseltine, J. N.; Sprengeler, P. A. Tetrahedron 1986, 42, 2957-2969.
25. (h) Haseltine, J.; Visnick, M.; Smith, A. B., III. J. Org. Chem. 1988, 53, 6160-6162.
26. (i) Smith, A. B., III; Haseltine, J. N.; Visnick, M. Tetrahedron 1989, 45, 2431-2449.
27. (j) Smith, A. B., III; Ohta, M.; Clark, W. M.; Leahy, J. W. Tetrahedron Lett. 1993, 34, 3033-3036.
28. (k) Smith, A. B., III; Nolen, E. G.; Shirai, R.; Blase, F. R.; Ohta, M.; Chida, N.; Hartz, R. A.; Fitch, D. M.; Clark, W. M.; Sprengeler, P. A. J. Org. Chem. 1995, 60, 7837-7848.
29. (l) Smith, A. B., III; Hartz, R. A.; Spoors, P. G.; Rainier, J. D. Isr. J. Chem. 1997, 37, 69-80.
30. (m) Smith, A. B., III; Kanoh, N.; Minakawa, N.; Rainier, J. D.; Blase, F. R.; Hartz, R. A. Org. Lett. 1999, 1, 1263-1266.
31. (n) Smith, A. B., III; Kanoh, N.; Ishiyama, H.; Hartz, R. A. J. Am. Chem. Soc. 2000, 122, 11254-11255.
32. Rivkin, A.; Nagashima, T.; Curran, D. P. Org. Lett. 2003, 5, 419-422.
33. For examples of gramine-type fragmentations, see: Brewster, J. H.; Eliel, E. L. Org. React. 1953, VII, 99-197.
34. Lactone (+)-14 can be prepared from commercially available (-)-Wieland-Miescher ketone in 16 steps and 8% overall yield.
35. (a) Stork, G.; Benaim, J. J. Am. Chem. Soc. 1971, 93, 5938-5939.
36. (b) Stork, G.; Benaim, J. Org. Synth. 1977, 57, 69-72.
37. A similar protocol had also proven effective in our paspalicine and paspalinine synthetic ventures.
38. For a review on the synthesis of indole derivatives, see: Sundberg, R. J. Indoles; Academic Press Inc.: San Diego, 1996.
39. Krüger, C.; Rochow, E. G.; Wannagat, U. Chem. Ber. 1963, 96, 2132-2137.
40. Grieco, P. A.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1976, 41, 1485-1486.
41. Sharpless, K. B.; Young, M. W. J. Org. Chem. 1975, 40, 947-949.
42. 24 polycycloalkanes to dodecahedrane and dimethyl dodecahedrane, see: Eaton, P. E. Tetrahedron 1979, 35, 2189-2223, and references therein.
43. See the Supporting Information for the experimental procedure.
44. Hartz, R. A. Ph.D. Thesis, University of Pennsylvania, 1996.
45. (a) Shunk, H.; Wilds, A. L. J. Am. Chem. Soc. 1949, 71, 3946-3950.
46. (b) Woodward, R. B.; Sondheimer, F.; Taub, D.; Heusler, K.; McLamore, W. M. J. Am. Chem. Soc. 1952, 74, 4223-4251.
47. (a) Semmler, W. Chem. Ber. 1892, 25, 3352-3354.
48. (b) Wolff, L. Annalen 1902, 322, 351-391.
49. (c) For a review of the transformation, see: Conley, R. T.; Chosh, S. In Mechanism of Molecular Migrations; Thyagarajin, B. S., Ed.; Interscience: New York, 1971; Vol. 4, pp 251-308.
50. With the fully elaborated coupling partners, the heteroatom Peterson olefination did not go to completion without external promoters such as silica gel or heating; see also ref 6e.
51. Parikh, J. R.; Doering, W. E. J. Am. Chem. Soc. 1967, 89, 5505-5507.
52. Attempts to use a MOM protecting group at C(25) as in the earlier model study failed due to our inability to differentiate the secondary and tertiary hydroxyls at C(25) and C(16), respectively.
53. Without the auxiliary hydrazone 37, we were unable to detect the desired coupling product between (+)-35 and (-)-15.
54. Intermediates (+)-38 and (+)-39 were both single isomers; the stereochemistry was not determined.
55. 3OD.
56. Grieco and co-workers exploited these conditions in an elegant synthesis of yuehchukene, see: (a) Grieco, P. A.; Clark, J. D.; Jagoe, C. T. J. Am. Chem. Soc. 1991, 113, 5488-5489. (b) Henry, K. J., Jr.; Grieco, P. A. J. Chem. Soc., Chem. Commun. 1993, 510-512.
57. Grieco and co-workers exploited these conditions in an elegant synthesis of yuehchukene, see: (a) Grieco, P. A.; Clark, J. D.; Jagoe, C. T. J. Am. Chem. Soc. 1991, 113, 5488-5489. (b) Henry, K. J., Jr.; Grieco, P. A. J. Chem. Soc., Chem. Commun. 1993, 510-512.
58. The major byproduct was a diene i (32% yield).
59. Nicolaou, K. C.; Hwang, C.-K.; Nugiel, D. A. J. Am. Chem. Soc. 1989, 111, 4136-4137.
60. Higher reaction temperature and/or longer reaction time resulted in over-reduction of the olefin in the side chain.
61. Dhaon, M. K.; Olsen, R. K.; Ramasamy, K. J. Org. Chem. 1982, 47, 1962-1965.
62. Nickon, A.; Mendelson, W. L. J. Org. Chem. 1965, 30, 2087-2089.
63. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
64. A similar autoxidation of an enol (ii) was observed by Kuwajima and co-workers during the synthesis of (+)-taxusin, see: Hara, R.; Furukawa, T.; Kashima, H.; Kusama, H.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1999, 121, 3072-3082. Equation presented
65. (a) House, H. O.; Tefertiller, B. A.; Olmstead, H. D. J. Org. Chem. 1968, 33, 935-942.
66. (b) Paquette, L, A.; Belmont, D. T.; Hsu, Y.-L. J. Org. Chem. 1985, 50, 4667-4672.
67. (c) Stereoselective Alkylation Reactions of Chiral Metal Enolates. Evans, D. A. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 3, Chapter 1, pp 1-110.
68. The lability of the TBS protecting group suggested that the use of the more robust TIPS ether would prove advantageous.
69. (a) Kobayashi, S.; Hachiya, I.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1993, 34, 3755-3758.
70. (b) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472-474.