Stereoselective construction of the dicyelopenta[a,d]cyclooctene core of the ceroplastin sesterterpenes by way of the anionic oxy-cope rearrangement

Journal of Organic Chemistry

Volumn 61, Issue 10, 1996, Pages 3268-3279

  Paquette, Leo A ^a   Liang, Shaowo ^a,b   Wang, Hui Ling ^a,c  

^a OHIO STATE UNIVERSITY   (United States)

^b EASTMAN CHEMICAL COMPANY   (United States)

^c NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

DICYCLOPENTA[A,D]CYCLO OCTANE DERIVATIVE; SESTERTERPENE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029927032     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952165+     Document Type: Article

References (48)

1. Present address: Eastman Chemical Company, Kingsport, TN.
2. On leave from the Department of Chemistry, National Tsing Hua University, Hsinshu 30043, Taiwan, Republic of China.
3. Kato, N.; Takeshita, H.; Kataoka, H.; Ohbuchi, S.; Tanaka, S. J. Chem. Soc., Perkin Trans. 1 1989, 165
4. (a) Rowley, M.; Tsukamoto, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735
5. (b) Rowley, M.; Kishi, Y. Tetrahedron Lett. 1988, 29, 4909.
6. Boeckman, R. K., Jr.; Arvanitis, A.; Voss, M. E. J. Am. Chem. Soc 1989, 111, 2737.
7. Paquette, L. A.; Wang, T.-Z., Vo, N. H. J Am. Chem. Soc. 1993, 115, 1676.
8. Okamoto, H.; Arita, H.; Kato, N.; Takeshita, H. Chem. Lett. 1994, 2335.
9. Paquette, L. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 609.
10. Wilson, S. R. Org. React. (N.Y.) 1993, 43, 93.
11. Preliminary communication: Paquette, L. A.; Liang, S.; Galatsis, P. Synlett 1990, 663.
12. Eilbracht, P.; Jelitte, R.; Trabold, P. Chem. Ber. 1986, 119, 169.
13. Tsuda, T.; Hayashi, T.; Satomi, H.; Kawamoto, T.; Saegusa, T. J. Org. Chem. 1986, 51, 537.
14. (a) Johnson, C. R.; Zeller, J. R. J. Am. Chem. Soc. 1982, 104, 4021.
15. (b) Johnson, C. R.; Schroeck, C. W.; Shanklin, J. R. J Am. Chem. Soc. 1973, 95, 7424.
16. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
17. Nicolaou, K. C.; Claremon, D. A.; Barnette, W. E.; Seitz, S. P. J Am. Chem. Soc. 1979, 107, 3704.
18. Reich, H. J ; Renga, J. M.; Reich, I. L. J. Am. Chem. Soc. 1975, 97, 5434.
19. Harding, K. E.; Clement, K. S. J. Org. Chem 1984, 49, 2049.
20. Barton, D. H.; Crich, D.; Kretzschmar, G. J. Chem. Soc., Perkin Trans 1 1986, 39.
21. Paquette, L. A.; Dahnke, K.; Doyon, J.; He W.; Wyant, K.; Friedrich, D. J. Org. Chem. 1991, 56, 6199.
22. Wulff, W. D.; Peterson, G A.; Bauta, W. E.; Chan, K.-S.; Faron, K. L.; Gilbertson, S. R.; Kaesler, R. W.; Yang, D. C.; Murray, C. K. J. Org. Chem. 1986, 51, 277.
23. (a) Berson, J. A. Acc Chem. Res. 1968, 1, 152.
24. (b) Berson, J. A.; Nelson, G. L. J. Am. Chem. Soc. 1967, 89, 5503.
25. (c) Roth, W. R.; Friedrich, A. Tetrahedron Lett. 1969, 2607.
26. (d) Masamune, S.; Takada, S.; Nakatsuka, N., Vukov, R.; Cain, E N. J. Am. Chem. Soc. 1969, 91, 4322.
27. Smith, A. B., III; Dunlap, N. K.; Sulikowski, G. A. Tetrahedron Lett. 1988, 29, 439.
28. Ponaras, A. A. Tetrahedron Lett. 1976, 3105
29. Kjeldsen, G.; Knudsen, J. S.; Raun-Petersen, L. S. Tetrahedron 1983, 39, 2237.
30. Lipshutz, B H.; Sengupta, S. Org. React. (N.Y.) 1992, 41, 135.
31. Agosta, W. C.; Wolff, S. J. Org. Chem. 1975, 40, 1699.
32. (a) Trost, B. M.; Buhlmayer, P.; Mao, M. Tetrahedron Lett. 1982, 23, 1443.
33. (b) Trost, B M.; Bernstein, P. R.; Funfschilling, P. C. J Am. Chem. Soc. 1979, 101, 4378.
34. Whitesell, J. K.; Matthews, R. S.; Minton, M. A.; Helbling, A. M. J. Am. Chem. Soc. 1981, 103, 3468.
35. (a) Gritter, R. J.; Wallace, T. J. J. Org.Chem. 1959, 24, 1051.
36. (b) Papadopoulos, E. P.; Jarrar, A.; Issidorides, C. H. J. Org. Chem. 1966, 31, 615.
37. Dollimore, D.; Tonge, K. H. J. Chem. Soc. B 1967, 1380.
38. Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873.
39. (a) Crisp, G. T.; Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 7500.
40. (b) Crisp, G T.; Scott, W. J. Synthesis 1985, 335.
41. Liang, S. Ph.D. Thesis, The Ohio State University, 1991.
42. Frey, H. M., Hopkins, R. G.; O'Neal, H. E.; Bond, P. T Chem. Commun. 1969, 1069.
43. Paquette, L. A.; Doyon, J. J. Am Chem. Soc. 1995, 117, 6799.
44. (a) Paquette, L. A.; Shi, Y.-J. J. Org. Chem. 1989, 54, 5205.
45. (b) Paquette, L. A.; Reagan, J.; Shreiber, S. L.; Teleha, C. A. J. Am. Chem. Soc. 1989, 111, 2331.
46. (c) Paquette, L. A.; Shi, Y.-J. J. Am. Chem. Soc. 1990, 112, 8478.
47. Eilbracht, P ; Hittinger, C.; Kufferath, K.; Schmitz, A.; Gilsing, H.-D. Chem. Ber. 1990, 123, 1089.
48. The authors have deposited the atomic coordinates for the X-ray structures with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, 1B2 IEZ, U.K.