First synthesis of cytotoxic 8,9-secokaurene diterpenoids. An enantioselective route to (-)-O-methylshikoccin and (+)- O-methylepoxyshikoccin

Journal of the American Chemical Society

Volumn 119, Issue 41, 1997, Pages 9662-9671

  Paquette, Leo A ^a   Backhaus, Dirk ^a   Braun, Ralf ^a   Underiner, Ted L ^a   Fuchs, Klaus ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENOID; O METHYLEPOXYSHIKOCCIN; O METHYLSHIKOCCIN; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030691768     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971527n     Document Type: Article

References (52)

1. Takeda, Y.; Fujita, T.; Ueno, A. Phytochemistry 1983, 22, 2531.
2. (a) Fujita, T.; Takeda, Y.; Shingu, T. Phytochemistry 1979, 18, 299.
3. (b) Fujita, T.; Takeda, Y.; Shingu, T.; Kido, M.; Taira, Z. J. Chem. Soc., Chem. Commun. 1982, 162.
4. (a) Node, M.; Ito, N.; Fuji, K.; Fujita, E. Chem. Pharm. Bull. 1982, 30, 2639.
5. (b) Node, M.; Ito, N.; Uchida, I.; Fujita, E.; Fuji, K. Chem. Pharm, Bull. 1985, 33, 1029.
6. Takeda, Y.; Ichihara, T.; Fujita, T.; Ueno, A. Chem. Pharm. Bull. 1989, 37, 1213.
7. (a) Fujita, E.; Ito, N.; Uchida. I.; Fuji, K.; Taga, T.; Osaki, K. J. Chem. Soc., Chem. Commun. 1979, 806.
8. (b) Taga, T.; Osaki, K.; Ito, N.; Fujita, E. Acta Cryst. 1982, B38, 2941.
9. Takeda, Y.; Futatsuishi, Y.; Matsumoto, T.; Terada, H.; Otsuka, H. Phytochemistry 1994, 35, 1289.
10. (a) Nagao, Y.; Ito, N.; Kohno, T.; Kuroda, H,; Fujita, E. Chem. Pharm. Bull 1982, 30, 727.
11. (b) Fuji, K.; Node, M.; Ito, N.; Fujita, E.; Takada, S.; Unemi, N. Chem. Pharm. Bull. 1985, 33, 1038.
12. Fuji, K.; Xu, H.-J.; Tatsumi, H.; Imahori, H.; Ito, N.; Node, M.; Inaba, M. Chem. Pharm. Bull. 1991, 39, 685.
13. Perry, N. B.; Burgess, E. J.; Tangney, R. S. Tetrahedron Lett. 1996, 37, 9387.
14. For an overview of our past research involving the synthesis of natural products endowed with bridgehead olefinic centers, consult Paquette, L. A. Chem. Soc. Rev. 1995, 24, 9.
15. (a) Paquette, L. A.; Ladouceur, G. J. Org. Chem. 1989, 54, 4278.
16. (b) Ladouceur, G.; Paquette, L. A. Synthesis 1992, 185.
17. Preliminary communication: Paquette, L. A.; Backhaus, D.; Braun, R. J. Am. Chem, Soc. 1996, 118, 11990.
18. re-recording(12) (a) Wieland, P.; Miescher, K. Helv. Chim. Acta 1950, 33, 2215. (b) Li, Y.; Bahman, N.; Crabbé, P. J. Chem. Soc., Perkin Trans, 1 1983, 2349. (c) Harada, N.; Sugioka, T.; Uda, H.; Kuriki, T. Synthesis 1990, 53. (d) Buchschacher, P.; Fürst, A. Org. Syn., Coll. Vol. 7 1990, 368.
19. re-recording(12) (a) Wieland, P.; Miescher, K. Helv. Chim. Acta 1950, 33, 2215. (b) Li, Y.; Bahman, N.; Crabbé, P. J. Chem. Soc., Perkin Trans, 1 1983, 2349. (c) Harada, N.; Sugioka, T.; Uda, H.; Kuriki, T. Synthesis 1990, 53. (d) Buchschacher, P.; Fürst, A. Org. Syn., Coll. Vol. 7 1990, 368.
20. re-recording(12) (a) Wieland, P.; Miescher, K. Helv. Chim. Acta 1950, 33, 2215. (b) Li, Y.; Bahman, N.; Crabbé, P. J. Chem. Soc., Perkin Trans, 1 1983, 2349. (c) Harada, N.; Sugioka, T.; Uda, H.; Kuriki, T. Synthesis 1990, 53. (d) Buchschacher, P.; Fürst, A. Org. Syn., Coll. Vol. 7 1990, 368.
21. re-recording(12) (a) Wieland, P.; Miescher, K. Helv. Chim. Acta 1950, 33, 2215. (b) Li, Y.; Bahman, N.; Crabbé, P. J. Chem. Soc., Perkin Trans, 1 1983, 2349. (c) Harada, N.; Sugioka, T.; Uda, H.; Kuriki, T. Synthesis 1990, 53. (d) Buchschacher, P.; Fürst, A. Org. Syn., Coll. Vol. 7 1990, 368.
22. Bauduin, G.; Pietrasanta, Y. Tetrahedron 1973, 29, 4225.
23. Kametani, T.; Suzuki, K.; Nemoto, H. J. Org. Chem. 1980, 45, 2204.
24. Woodward, R. B.; Patchett, A. A.; Barton, D. H. R.; Ives, D. A. J.; Kelly, R. B. J. Am. Chem. Soc. 1954, 76, 2852.
25. (a) Schmidt, C.; Kokosi, J. Synth. Commun. 1985, 15, 341.
26. (b) Ciceri, P.; Denmitz, F. W. J. Tetrahedron Lett. 1997, 38, 389.
27. (a) Corey, E. J.; Fleet, G. W. J. Tetrahedron Lett. 1973, 4459.
28. (b) Wright, J.; Drtina, G. J.; Roberts, R. A.; Paquette, L. A. J. Am. Chem. Soc. 1988, 110, 5806.
29. (a) Jones, G. Org. React. 1967, 15, 204.
30. (b) Bolte, M. L.; Crow, W. D.; Yoshida, S. Aust. J. Chem. 1982, 35, 1421.
31. Hobel, K.; Margaretha, P. Helv. Chim. Acta 1989, 72, 975.
32. Nagarajan, K.; Shenoy, S. J. Ind. J. Chem., Sect. B 1992, 31, 73.
33. Fuchs, K.; Paquette, L. A. J. Org. Chem. 1994, 59, 528.
34. (a) Drauz, K.; Kleemann, A.; Samson, M. Chem. Ztg. 1984, 108, 391.
35. (b) Kleemann, A.; Samson. M. Eur. Pat. Appl. EP 52,200, May 26, 1982; Chem. Abstr. 1982, 97, 163497j.
36. N2 displacement by cyanide ion on β-bromoacetaldehyde dimethylacetal.
37. Lipshutz, B. H.; Harvey, D. F. Synth. Commun. 1982, 72, 267.
38. Detty, M. R. J. Org. Chem. 1980, 45, 274.
39. House, H. O.; Lubinkowski, J.; Good, J. J. J. Org. Chem. 1975, 40, 86.
40. Gilbert, J. C; Senaratne, K. P. A. Tetrahedron Lett. 1984, 25, 2303.
41. (a) Evans, D. A.; Sims, C. L.; Andrews, G. C. J. Am. Chem. Soc. 1977, 99, 5453.
42. (b) Mander, L. N.; Turner, J. V. Aust. J. Chem. 1980, 33, 1559.
43. Martin, S. F.; Dodge, J. A. Tetrahedron Lett. 1991, 32, 3017.
44. Martin, S. F.; Rüeger, H.; Williamson, S. A.; Grzejzczak, S. J. Am. Chem. Soc. 1987, 109, 6124.
45. (a) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
46. (b) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 55, 2899.
47. (a) Holy, N.; Fowler, R.; Burnett, E.; Lorenz, R. Tetrahedron 1979, 35, 613.
48. (b) Caputo, R.; Ferreri, C; Mastroianni, D.; Palumbo, G.; Wenkert, E. Synth. Commun. 1992, 22, 2305.
49. Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885.
50. 3 (δ 3.26) were erroneously claimed to appear at δ 3.34 and 3.18, respectively. The spectra graciously provided by the Japanese group and our re-recording of these data revealed the source of the confusion to be typographical.
51. Backhaus, D.; Paquette, L. A. Tetrahedron Lett, 1997, 38, 29.
52. For general experimental procedures, see: Wang, T.-Z.; Pinard, E.; Paquette, L. A. J. Am. Chem. Soc. 1996, 118, 1309.