Formal total synthesis of (+)-diepoxin σ

Journal of Organic Chemistry

Volumn 65, Issue 20, 2000, Pages 6319-6337

  Wipf, Peter ^a   Jung, Jae Kyu ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; ANTINEOPLASTIC AGENT; BORON; DIEPOXIN; LIGAND; MK 3018; NAPHTHALENE; NAPHTHAZARIN; NATURAL PRODUCT; SCH 49209; SCH 49210; SCH 49211; SCH 49212; SCH 50673; SCH 50676; SCH 53514; SCH 53516; SCH 53823; SCH 53825; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; OXYGENATION; REACTION ANALYSIS;

AFRICA; CRYSTALLOGRAPHY, X-RAY; EPOXY COMPOUNDS; PLANTS, MEDICINAL; SPIRO COMPOUNDS;

EID: 0034613228     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000684t     Document Type: Article

References (68)

1. Ogishi, H.; Chiba, N.; Mikawa, T.; Sasaki, T.; Miyaji, S.; Sezaki, M. JP 01,294,686, 1989; Chem. Abstr. 1990, 113, 38906q.
2. (a) Connolly, J. D. 4th International Symposium and Pakistan-US. Binational Workshop on Natural Products Chemistry, Karachi, Pakistan, 1990.
3. (b) Connolly, J. D. Structural elucidation of some natural products. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science Publishers E.V.: Amsterdam, 1991; Vol. 9, pp 256-258.
4. (a) Krohn, K.; Michel, A.; Flörke, U.; Aust, H.-J.; Draeger, S.; Schulz, B. Liebigs Ann. Chem. 1994, 1093.
5. (b) Krohn, K.; Michel, A.; Flörke, U.; Aust, H.-J.; Draeger, S.; Schulz, B. Liebigs Ann. Chem. 1994, 1099.
6. (a) Weber, H. A.; Baenziger, N. C.; Gloer, J. B. J. Am. Chem. Soc. 1990, 112, 6718.
7. (b) Preussomerins A-F: Weber, H. A.; Gloer, J. B. J. Org. Chem. 1991, 56, 4355.
8. Polish J. D.; Dombrowski, A. W.; Tsou, N. N.; Salituro, G. M.; Curotto, J. E. Mycologia 1993, 85, 62.
9. Singh, S. B.; Zink, D. L.; Liesch, J. M.; Ball, R. G.; Goetz, M. A.; Bolessa, E. A.; Giacobbe, R. A.; Silverman, K. C.; Bills, G. F.; Pelaez, F.; Cascales, C.; Gibbs, J. B.; Lingham, R. B. J. Org. Chem. 1994, 59, 6296.
10. Schlingmann, G.; West, R. R.; Milne, L.; Pearce, C. J.; Carter, G. T. Tetrahedron Lett. 1993, 34, 7225.
11. Schlingmann, G.; Matile, S.; Berova, N.; Nakanishi, K.; Carter, G. T. Tetrahedron 1996, 52, 435.
12. Chu, M.; Truumees, I.; Patel, M. G.; Gullo, V. P.; Puar, M. S.; McPhail, A. T. J. Org. Chem. 1994, 59, 1222
13. Chu, M.; Truumees, I.; Patel, M. G.; Gullo, V. P.; Blood, C.; King, I.; Pai, J.-K.; Puar, M. S. Tetrahedron Lett. 1994, 35, 1343.
14. (a) Thiergardt, R.; Hug, P.; Rihs, G.; Peter, H. H. Tetrahedron Lett. 1994, 35, 1043.
15. (b) Petersen, F.; Moerker, T.; Vanzanella, F.; Peter, H. H. J. Antibiot. 1994, 47, 1098.
16. (c) Thiergardt, R.; Rihs, G.; Hug, P.; Peter, H. H. Tetrahedron 1995, 51, 733.
17. (a) Chu, M.; Truumees, I.; Patel, M. G.; Gullo, V. P.; Pai, J.-K.; Das, P. R.; Puar, M. S. Bioorg. Med. Chem. Lett. 1994, 4, 1539.
18. (b) Chu, M.; Truumees, I.; Patel, M.; Blood, C.; Das, P. R.; Puar, M. S. J. Antibiot. 1995, 48, 329.
19. Chu, M.; Patel, M. G.; Pai, J.-K.; Das, P. R.; Puar, M. S. Bioorg. Med. Chem. Lett. 1996, 6, 579.
20. McDonald, L. A.; Abbanat, D. R.; Barbieri, L. R.; Bernan, V. S.; Discafani, C. M.; Greenstein, M.; Janota, K.; Korshalla, J. D.; Lassota, P.; Tischler, M.; Carter, G. T. Tetrahedron Lett. 1999, 40, 2489.
21. Krohn, K.; Beckmann, K.; Aust, H.-J.; Draeger, S.; Schulz, B.; Busemann, S.; Bringmann, G. Liebigs Ann./Recl. 1997, 2531.
22. Wipf, P.; Jung, J.-K. Angew. Chem., Int. Ed. Engl. 1997, 36, 764.
23. Barrett, A. G. M.; Hamprecht, D.; Meyer, T. Chem. Commun. 1998, 809.
24. Ragot, J. P.; Alcarez, M.-L.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 4921.
25. Wipf, P.; Jung, J.-K. J. Org. Chem. 1998, 63, 3530.
26. Arai, S.; Oku, M.; Miura, M.; Shioiri, T. Synlett 1998, 1201.
27. Wipf, P.; Jung, J.-K. J. Org. Chem. 1999, 64, 1092.
28. Ragot, J. P.; Steeneck, C.; Alcarez, M.-L.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1999, 1073.
29. Chi, S.; Heathcock, C. H. Org. Lett. 1999, 1, 3.
30. Graybill, B. M.; Shirley, D. A. J. Org. Chem. 1966, 31, 1221.
31. (a) Moore, J. A.; Rahm, M. J. Org. Chem. 1961, 26, 1109.
32. (b) Watanabe, M.; Maenosono, H.; Furukawa, S. Chem. Pharm. Bull. 1983, 31, 2662.
33. Moroz, A. A.; Shvartsberg, M. S. Russ. Chem. Rev. 1974, 43, 679.
34. Wipf, P.; Kim, Y. Tetrahedron Lett. 1992, 33, 5477.
35. (a) Pelter, A.; Elgendy, S. Tetrahedron Lett. 1988, 29, 677-680.
36. (b) Tamura, Y.; Yakura, T.; Haruta, J.; Kita, Y. J. Org. Chem. 1987, 52, 3927.
37. Energy-minimized conformations shown in Figure 7 were obtained by Monte Carlo conformer searching with MacroModel (v. 5.5; Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440). The lowest energy conformations were further optimized with Spartan (v. 5.1.1; Wavefunction, Inc., Irvine, CA) at the HF 6-31G* level.
38. (a) Back, T. G. J. Org. Chem. 1981, 46, 1442.
39. (b) Zoretic, P. A.; Chambers, R. J. J. Org. Chem. 1985, 50, 2981.
40. Wipf, P.; Jung, J.-K.; Rodriguez, S.; Lazo, J. S. Tetrahedron, in press.
41. Jung, J.-K. Ph.D. Thesis, University of Pittsburgh, 1999.
42. Laatsch, H. Liebigs Ann. Chem. 1990, 1151.
43. Greene, T. W.; Wuts, P. G. M. Protective groups in organic synthesis, 2nd ed.; Wiley: New York, 1991.
44. (a) Mann, F. G.; Pragnell, M. J. J. Chem. Soc. 1965, 4120.
45. (b) Ireland, R. E.; Walba, D. M. Org. Synth. 1977, 56, 44.
46. 3) δ 9.55 (s, 1 H, OH), 7.57-7.41 (m, 4 H), 7.10 (dd, 1 H, J = 7.6, 0.9 Hz), 6.91 (d, 1 H, J = 7.9 Hz), 6.88 (d, 1 H, J = 10.5 Hz), 6.71 (d, 1 H, J = 10.7 Hz), 6.60 (dd, 1 H, J = 10.2, 8.2 Hz), 6.17 (d, 1 H, J = 10.3 Hz), 5.92-5.87 (m, 1 H), 5.50-5.46 (m, 1 H), 4.21-4.07 (m, 2 H), 2.88 (q, 1 H, J = 4.2 Hz), 2.80-2.67 (m, 1 H), 2.47-2.35 (m, 1 H). These data indicate the presence of a trifluoroethoxy group and a phenol moiety, but the structure was not fully assigned.
47. (a) Rickborn, B. Org. React. 1998, 52, 1.
48. (b) Rickborn, B. Org. React. 1998, 53, 223.
49. (c) Ichihara, A.; Kobayashi, M.; Oda, K.; Sakamura, S.; Sakai, R. Tetrahedron 1979, 35, 2861.
50. (d) Kamikubo, T.; Hiroya, K.; Ogasawara, K. Tetrahedron Lett. 1996, 37, 499.
51. (e) Weinmann, H.; Winterfeldt, E. Synthesis 1996, 357.
52. (f) Stork, G.; La Clair, J. J.; Spargo, P.; Nargund, R. P.; Totah, N. J. Am. Chem. Soc. 1996, 118, 5304.
53. (g) Bunnage, M. E.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1110.
54. (h) Bunnage, M. E.; Nicolaou, K. C. Eur. J. Chem. 1997, 3, 187.
55. Ichihara, A.; Kimura, R.; Oda, K.; Sakamura, S. Tetrahedron Lett. 1976, 4741.
56. Kamikubo, T.; Ogasawara, K. Chem. Commun. 1996, 1679.
57. Kelly, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc. 1986, 108, 3510.
58. Maruoka, K.; Sakurai, M.; Fujiwara, J.; Yamamoto, H. Tetrahedron Lett. 1986, 27, 4895.
59. Lingenfalter, D. S.; Helgeson, R. C.; Cram, D. J. J. Org. Chem. 1981, 46, 393.
60. Cai, D.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7991.
61. (a) Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 49, 1958.
62. (b) Cotton, F. A.; Faut, O. D.; Goodgame, M. L. J. Am. Chem. Soc. 1961, 83, 344.
63. Hafelinger, G.; Hack, F.; Westermayer, G. Chem. Ber. 1978, 111, 1323.
64. Holloway, H. E.; Nauman, R. V.; Wharton, J. H. J. Phys. Chem. 1968, 72, 4468.
65. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
66. Simonsen, K. B.; Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 7536.
67. The absolute configuration of (+)-33 was assigned in accordance with ref 40.
68. Newhall, W. F.; Harris, S. A.; Holly, F. W.; Johnston, E. L.; Richter, J. W.; Walton, E.; Wilson, A. N.; Folkers, K. J. Am. Chem. Soc. 1955, 77, 5646.