Total synthesis of the sesquiterpenoid polyols (±)-euonyminol and (±)-3,4-dideoxymaytol, core constituents of esters of the Celastraceae

Journal of the American Chemical Society

Volumn 119, Issue 10, 1997, Pages 2404-2419

  White, James D ^a   Shin, Hyunik ^a   Kim, Tae Seong ^a   Cutshall, Neil S ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIDEOXYMAYTOL; EUONYMINOL; POLYOL; SESQUITERPENOID; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0031003907     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963567h     Document Type: Article

References (55)

1. Kuo, Y.-H.; King, M. L.; Chen, C.-F.; Chen, H.-Y.; Chen, C.-H.; Chen, K.; Lee, K.-H. J. Nat. Prod. 1994, 57, 263.
2. Takaishi, Y.; Ujita, K.; Tokuda, H.; Nishino, H.; Iwashima, A.; Fujita, T. Cancer Lett. 1992, 65, 19.
3. Zheng, Y. L.; Xu, Y.; Lin, J. F. Acta Pharm. Sin. 1989, 24, 568.
4. (a) Gonzalez, A. G.; Jimenez, I. A.; Ravelo, A. G.; Belles, X.; Piulachs, M. D. Biochem. Syst. Ecol. 1992, 20, 311.
5. (b) Gonzalez, A. G.; Jimenez, I. A.; Ravelo, A. G.; Bazzocchi, I. L. Tetrahedron 1993, 49, 6637.
6. Kupchan, S. M.; Smith, R. M.; Bryan, R. F. J. Am. Chem. Soc. 1970, 92, 6667.
7. Baudouin, G.; Tillequin, F.; Koch, M. Heterocycles 1984, 22, 2221.
8. (a) Sugiura, K.; Shizuri, Y.; Wada, H.; Yamada, K.; Hirata, Y. Tetrahedron Lett. 1971, 2733.
9. (b) Han, B. H.; Park, M. M.; Ryu, J. R.; Park J. H.; Naoki, H. Phytochemistry 1990, 29, 2303.
10. (c) Beroza, M. J. Am. Chem. Soc. 1951, 73, 3656.
11. (d) Kuo, Y.-H.; Chen, C.-H.; Kuo, L.-M.; King, M.-L.; Wu, T.-S.; Lu, S.-T.; Chen, I.-S.; McPhail, D. R.; McPhail, A. T.; Lee, K.-H. Heterocycles 1989, 29, 1465.
12. (a) Baxter, R. L.; Crombie, W. M. L.; Crombie, L.; Simmonds, D. J.; Whiting, D. A.; Szendrei, K. J. Chem. Soc., Perkin Trans. I 1979, 2982.
13. (b) Baxter, R. L.; Crombie, L.; Simmonds, D. J.; Whiting, D. A. J. Chem. Soc., Perkin Trans. I 1979, 2972.
14. (c) Crombie, L.; Crombie, W. M. L.; Whiting, D. A.; Szendrei, K. J. Chem Soc., Perkin Trans. I 1979, 2976.
15. Crombie, L.; Toplis, D.; Whiting, D. A.; Rozsá, Z.; Hahmann, J.; Szendrei, K. J. Chem. Soc., Perkin Trans. I 1986, 531.
16. (a) Legras, M.; Fretillere, Y. Med. Trop. 1965, 25, 720.
17. (b) Getahun, A.; Krikorian, A. D. Econ. Bot. 1973, 27, 353.
18. Begley, M. J.; Crombie, L.; Fleming, R. A.; Whiting, D. A.; Rozsá, Z.; Kelenyi, M.; Hohmann, J.; Szendrei, K. J. Chem. Soc., Perkin Trans. I 1986, 535.
19. Crombie, L.; Crombie, W. M. L.; Whiting, D. A. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1990; Vol. 39, pp 139-164.
20. (a) Sugiura, K.; Yamada, K.; Hirata, Y. Tetrahedron Lett. 1973, 113.
21. (b) Sasaki, K.; Hirata, Y. J. Chem. Soc., Perkin Trans. II 1972, 1268.
22. (c) Shizuri, Y.; Wada, H.; Sugiura, K.; Yamda, K.; Hirata, Y. Tetrahedron 1973, 29, 1773.
23. (d) Taylor, I. F., Jr.; Watson, W. H. Acta Crystallogr. 1977, B33, 317.
24. For earlier accounts see: (a) White, J. D. Pure Appl. Chem. 1994, 66, 2183. (b) White, J. D.; Cutshall, N. S.; Kim, T-S.; Shin, H. J. Am. Chem. Soc. 1995, 117, 9780.
25. For earlier accounts see: (a) White, J. D. Pure Appl. Chem. 1994, 66, 2183. (b) White, J. D.; Cutshall, N. S.; Kim, T-S.; Shin, H. J. Am. Chem. Soc. 1995, 117, 9780.
26. Mander, L. N.; Sethi, S. P. Tetrahedron Lett. 1984, 25, 5953.
27. Kraus, G. A.; Taschner, M. J. J. Org. Chem. 1980, 45, 1175.
28. Gemal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1978, 100, 2226.
29. (a) Henbest, H. B.; Wilson, R. A. J. Chem. Soc. 1957, 1958.
30. (b) Berti, G. Top. Stereochem. 1973, 9, 93.
31. (c) Hirayama, M.; Gamoh, K.; Ikeyama, N. Tetrahedron Lett. 1982, 23, 4725.
32. (a) Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1557.
33. (b) Masaki, Y.; Hashimoto, K.; Serizawa, Y.; Koji, K. Bull. Chem. Soc. Jpn. 1984, 57, 3476.
34. For mechanistic speculation regarding variations in stereoselectivity in organocopper additions to carbocyclic enones in the presence of trimethylsilyl chloride, see: (a) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015. (b) Horiguchi, Y.; Komatu, M.; Kuwajima, I. Tetrahedron Lett. 1989, 30, 7087. (c) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1990, 31, 1393. (d) Corey, E. J.; Boaz, N. W. Tetrahedron 1989, 45, 545.
35. For mechanistic speculation regarding variations in stereoselectivity in organocopper additions to carbocyclic enones in the presence of trimethylsilyl chloride, see: (a) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015. (b) Horiguchi, Y.; Komatu, M.; Kuwajima, I. Tetrahedron Lett. 1989, 30, 7087. (c) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1990, 31, 1393. (d) Corey, E. J.; Boaz, N. W. Tetrahedron 1989, 45, 545.
36. For mechanistic speculation regarding variations in stereoselectivity in organocopper additions to carbocyclic enones in the presence of trimethylsilyl chloride, see: (a) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015. (b) Horiguchi, Y.; Komatu, M.; Kuwajima, I. Tetrahedron Lett. 1989, 30, 7087. (c) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1990, 31, 1393. (d) Corey, E. J.; Boaz, N. W. Tetrahedron 1989, 45, 545.
37. For mechanistic speculation regarding variations in stereoselectivity in organocopper additions to carbocyclic enones in the presence of trimethylsilyl chloride, see: (a) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015. (b) Horiguchi, Y.; Komatu, M.; Kuwajima, I. Tetrahedron Lett. 1989, 30, 7087. (c) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1990, 31, 1393. (d) Corey, E. J.; Boaz, N. W. Tetrahedron 1989, 45, 545.
38. Hunig, S.; Wehner, G. Synthesis 1975, 181.
39. (a) Toromanoff, E. Bull. Soc. Chim. Fr. 1962, 708.
40. (b) Deslongchamps, P. In Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, 1983; pp 221-231.
41. (a) Solomon, M.; Jamison, C. L.; McCormick, M.; Liotta, D. C.; Cherry, D. A.; Mills, J. E.; Shah, R. D.; Rodgers, J. D.; Maryanoff, C. A. J. Am. Chem. Soc. 1988, 110, 3702.
42. (b) Swiss, K. A.; Liotta, D. C.; Maryanoff, C. A. J. Am. Chem Soc. 1990, 112, 9393.
43. (c) Swiss, K. A.; Hinkley, W.; Maryanoff, C. A.; Liotta, D. C. Synthesis 1992, 127.
44. Barrett, H. C.; Büchi, G. J. Am. Chem. Soc. 1967, 89, 5665.
45. (a) Thompson, H. W. J. Org. Chem. 1971, 36, 2577.
46. (b) Thompson, H. W.; McPherson, E.; Lences, B. L. J. Org. Chem. 1976, 41, 2903.
47. Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol 3, Chapter 6.
48. Attempts to effect substitution of the iodo group of 54 using potassium Superoxide or cesium acetate afforded a crystalline cyclobutane resulting from initial formation of the ketone enolate followed by intramolecular displacement of iodide. The structure of the cyclobutane was confirmed by X-ray crystallographic analysis, proving that the major product from 52 possessed an endo iodomethyl substituent.
49. Günther, H. In NMR Spectroscopy; Wiley: Chichester, U.K., 1995; pp 124-125.
50. Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136.
51. Arjona, O.; de Dios, A.; Plumet, J.; Saez, B. J. Org. Chem. 1995, 60, 4932.
52. Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703.
53. Speck, J. C. Adv. Carbohydr. Chem. 1958, 13, 63.
54. Kofron, W. G.; Baclawski, L. M. J. Org. Chem. 1976, 41, 1876.
55. Still, W. C.; Kahn, M.; Mitra, A. J. J. Org. Chem. 1978, 43, 2923.