Base-Induced Rearrangement of Perhydronaphthalene-1,4-diol Monosulfonate Esters to 11-Oxatricyclo[5.3.1.02,6]undecanes. Total Synthesis of Furanether B

Journal of Organic Chemistry

Volumn 63, Issue 1, 1998, Pages 122-128

  Bell, Roel P L ^a   Sobolev, Arkadij ^a   Wijnberg, Joannes B P A ^a   De Groot, Aede ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002470977     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971545n     Document Type: Article

References (59)

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9. + as the counterion will be diminished. Also, see ref 1b.
10. (a) Battaglia, R.; De Bernardi, M.; Fronza, G.; Mellerio, G.; Vidari, G.; Vita-Finzi, P. J. Nat. Prod. 1980, 43, 319.
11. For an extensive review of lactarane sesquiterpenes, see: (b) Vidari, G.; Vita-Finzi, P. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1995; Vol. 17, pp 153-206.
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16. Heathcock, C. H.; Gray, D. Tetrahedron 1971, 27, 1239.
17. 1b a relatively large quantity of 1 was available.
18. + as counterion; see ref 4.
19. For example, see: Harada, N.; Sugioka, T.; Uda, H.; Kuriki, T. synthesis 1990, 53 and references therein.
20. Torii, S.; Okumoto, H., Nakayasu, S.; Kotani, T. Chem. Lett. 1989, 1975.
21. Dragovich, P. S.; Prins, T. J.; Zhou, R. J. Org. Chem. 1995, 60, 4922.
22. (a) Paulsen, H.; Eberstein, K.; Koebernick, W. Tetrahedron Lett. 1974, 4377.
23. (b) Rennecke, R.-W.; Eberstein, K.; Köll, P. Chem. Ber. 1975, 108, 3652.
24. McChesney, J. D.; Wycpalek, A. F. J. Chem. Soc., Chem. Commun. 1971, 542.
25. (a) Bull, J. R.; Lachmann, H. H. Tetrahedron Lett. 1973, 3055.
26. (b) Szajewski, R. P. J. Org. Chem. 1978, 43, 1819.
27. 3AlH is known to reduce ketones selectively in the presence of ester functions, see: Levine, S. G.; Eudy, N. H. J. Org. Chem. 1970, 35, 549.
28. 3AlH would proceed from the less sterically hindered α side.
29. As a minor side reaction, some elimination of the acetate group had taken place.
30. The alcohol 18 was also produced by treatment of 14 with LAH in refluxing toluene, but the yield of this reaction only amounted to 30%.
31. (a) de Groot, A.; Jansen, B. J. M. J. Org. Chem. 1984, 49, 2034.
32. (b) Jansen, B. J. M.; Bouwman, C. T.; de Groot, A. Tetrahedron Lett. 1994, 35, 2977.
33. For a review of the Pummerer reaction, see: DeLucchi, O; Miotti, U.; Modena, G. Org. React. 1991, 40, 157.
34. The formylation procedure described in ref 7a gave 20 in only 42% yield.
35. 7a of 21 to furanether B could not be achieved in acceptable yield.
36. (a) Corey, E. J.; Seebach, D. J. Org. Chem. 1966, 31, 4097.
37. (b) Ager, D. J. J. Chem. Soc., Perkin Trans. 1 1983, 1131.
38. A similar protocol has proven to be successful in the synthesis of annulated drimane sesquiterpenes; see ref 23.
39. For a relevant report on organocerium reagents, see: Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
40. 2-assisted hydrolysis to 22 proceeded smoothly without using acid.
41. Greeves, N.; Lyford, L. Tetrahedron Lett. 1992, 33, 4759.
42. Leonard, N. J.; Johnson, C. R. J. Org. Chem. 1962, 27, 282.
43. Sharma, A. K.; Swern, D. Tetrahedron Lett. 1974, 1503.
44. Jommi, G.; Pagliarin, R.; Sisti, M.; Tavecchia, P. Synth. Commun. 1989, 19, 2467.
45. +) 436.1320, found 436.1321.
46. After being dried, the solution was concentrated under reduced pressure at -15 °C. If the solution was concentrated at room temperature, considerable amounts of 25 were detected in the remaining product mixture.
47. +, 9), 219 (23), 205 (35), 187 (22), 152 (43), 123 (39), 107 (40), 95 (51), 77 (50), 43 (100).
48. Lactarane dialdehydes are supposed to be highly reactive compounds, see: Sterner, O., Ph.D. Thesis, University of Lund, 1985.
49. Jansen, B. J. M., Ph.D. Thesis, Wageningen Agricultural University, 1993.
50. At room temperature, the reaction took more than 2 weeks to achieve completion.
51. The chromatographic separation of 31 and 32 appeared to be problematic.
52. Stable O,S-ketals formed in Pummerer rearrangements have been reported. For example, see: (a) Hatch, R. P.; Shringarpure, J.; Weinreb, S. M. J. Org. Chem. 1978, 43, 4172. (b) Padwa, A.; Kappe, C. O.; Cochran, J. E.; Snyder, J. P. J. Org. Chem. 1997, 62, 2786.
53. Stable O,S-ketals formed in Pummerer rearrangements have been reported. For example, see: (a) Hatch, R. P.; Shringarpure, J.; Weinreb, S. M. J. Org. Chem. 1978, 43, 4172. (b) Padwa, A.; Kappe, C. O.; Cochran, J. E.; Snyder, J. P. J. Org. Chem. 1997, 62, 2786.
54. The reaction was performed with 24 obtained from the incomplete reaction of 23 with 1 equiv of TFAA and 2,6-lutidine.
55. 3.
56. 1H NMR spectrum, 20 most likely consisted of a ca. 9:1 mixture of the intramolecularly hydrogen-bonded Z-isomer (one-proton singlet at δ 7.52) and the keto aldehyde form (one-proton singlet at δ 9.58), respectively. Also, see ref 7a.
57. A solution of lithiated thioanisole (0.49 M in ether) was prepared by the following procedure. To a stirred solution of 0.9 mL (7.67 mmol) of thioanisole in 10 mL of ether was added 4.8 mL (7.68 mmol) of n-BuLi (1.6 M in hexane). The solution was heated at reflux temperature for 15 h and then cooled to rt.
58. GC analysis revealed the presence of small amounts (<5%) of 25 and 26.
59. 2 and 4 M aqueous HCl at 35 °C.