Stereospecific Synthesis of 1,6-Dioxadecalins and 2,2′-Linked Ditetrahydrofurans by Rearrangement of Steroidal Spiroacetals

Journal of Organic Chemistry

Volumn 63, Issue 18, 1998, Pages 6355-6362

  Betancor, Carmen ^b   Dorta, Rosa L ^b   Freire, Raimundo ^a   Martín, Angeles ^a   Prangé, Thierry ^c   Suárez, Ernesto ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

^b UNIVERSIDAD DE LA LAGUNA   (Spain)

^c UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; DECALIN DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; MOLECULAR DYNAMICS; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0032483561     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980834o     Document Type: Article

References (48)

1. (a) Martín, A.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1995, 36, 4489-4492.
2. (b) Dorta, R. L.; Martín, A.; Salazar, J. A.; Suárez, E.; Prangé, T. Tetrahedron Lett. 1996, 37, 6021-6024.
3. (c) Dorta, R. L.; Martín, A.; Suárez, E.; Prange, T. Tetrahedron: Asymmetry 1996, 7, 1907-1910.
4. (d) Martín, A.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1996, 61, 3999-4006.
5. (e) Dorta, R. L.; Martín, A.; Salazar, J. A.; Suárez, E.; Prangé, T. J. Org. Chem. 1998, 63, 2251-2261.
6. (a) Vaillancourt, V.; Praft, N. E.; Perron, F.; Albizati, K. F. In The Total Synthesis of Natural Products, Vol. 8; ApSimon, J., Ed.; Wiley: New York, 1992; pp 533-691.
7. (b) Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617-1661.
8. (c) Boivin, T. L. B. Tetrahedron 1987, 43, 3309-3362.
9. (d) Kluge, A. F. Heterocycles 1986, 24, 1699-1740.
10. (a) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897-1909.
11. (b) Hall, J. G.; Reiss, J. A. Aust. J. Chem. 1986, 39, 1401-1409.
12. (c) Hoffmann, R. W.; Münster, I. Tetrahedron Lett. 1995, 36, 1431-1434.
13. (d) Murata, M.; Iwashita, T.; Yokoyama, A.; Sasaki, M.; Yasumoto, T. J. Am. Chem. Soc. 1992, 114, 6594-6596.
14. (e) Murata, M.; Naoki, H.; Iwashita, T.; Matsunaga, S.; Sasaki, M.; Yokoyama, A.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 2060-2062.
15. (f) Sasaki, M.; Nonomura, T.; Murata, M.; Tachibana, K. Tetrahedron Lett. 1994, 35, 5023-5026.
16. (g) Uemura, D.; Takahashi, K.; Yamamoto, T.; Katayama, C.; Tanaka, J.; Okumura, Y.; Hirata, Y. J. Am. Chem. Soc. 1985, 107, 4796-4798.
17. (h) Hirata, Y.; Uemura, D. Pure Appl. Chem. 1986, 58, 701-710.
18. (a) Aicher, T. D.; Buszek, K. R.; Fang, F. G.; Forsyth, C. J.; Jung, S. H.; Kishi, Y.; Matelich, M. C.; Scola, P. M.; Spero, D. M.; Yoon, S. K. J. Am. Chem. Soc. 1992, 114, 3162-3164.
19. (b) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato, M.; Untersteller, E.; Xiao, X.-Y. J. Am. Chem. Soc. 1995, 117, 1171-1172.
20. (c) Nicolaou, K. C.; Rutjes, F. P. J. T.; Theodorakis, E. A.; Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 1173-1174 and references cited.
21. (a) Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Eds.; Springer Chemistry: Wienna, 1997; Vol. 70, pp 81-288.
22. (b) Koert, U. Synthesis 1995, 115-132. See also: Beauchamp, T. J.; Powers, J. P.; Rychnovsky, S. D. J. Am. Chem. Soc. 1995, 117, 12873-12874.
23. (b) Koert, U. Synthesis 1995, 115-132. See also: Beauchamp, T. J.; Powers, J. P.; Rychnovsky, S. D. J. Am. Chem. Soc. 1995, 117, 12873-12874.
24. For reviews on polyether antibiotics see: (a) Polyether Antibiotics: Naturally Occurring Acid Ionophores; Westley, J. W., Ed.; Marcel Dekker: New York, 1982; Vols. 1 and 2. (b) Wierenga, W. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley: New York, 1992; Vol. 4, pp 263-351. For recent syntheses see: (c) Ireland, R. E.; Armstrong, J. D., III.; Leberton, J.; Meissner, R. S.; Rizzacasa, M. A. J. Am. Chem. Soc. 1993, 115, 7152-7156. (d) Ireland, R. E.; Meissner, R. S.; Rizzacasa, M. A. J. Am. Chem. Soc. 1993, 115, 7166-7172. (e) Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. J. Am. Chem. Soc. 1995, 117, 3448-3467.
25. For reviews on polyether antibiotics see: (a) Polyether Antibiotics: Naturally Occurring Acid Ionophores; Westley, J. W., Ed.; Marcel Dekker: New York, 1982; Vols. 1 and 2. (b) Wierenga, W. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley: New York, 1992; Vol. 4, pp 263-351. For recent syntheses see: (c) Ireland, R. E.; Armstrong, J. D., III.; Leberton, J.; Meissner, R. S.; Rizzacasa, M. A. J. Am. Chem. Soc. 1993, 115, 7152-7156. (d) Ireland, R. E.; Meissner, R. S.; Rizzacasa, M. A. J. Am. Chem. Soc. 1993, 115, 7166-7172. (e) Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. J. Am. Chem. Soc. 1995, 117, 3448-3467.
26. For reviews on polyether antibiotics see: (a) Polyether Antibiotics: Naturally Occurring Acid Ionophores; Westley, J. W., Ed.; Marcel Dekker: New York, 1982; Vols. 1 and 2. (b) Wierenga, W. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley: New York, 1992; Vol. 4, pp 263-351. For recent syntheses see: (c) Ireland, R. E.; Armstrong, J. D., III.; Leberton, J.; Meissner, R. S.; Rizzacasa, M. A. J. Am. Chem. Soc. 1993, 115, 7152-7156. (d) Ireland, R. E.; Meissner, R. S.; Rizzacasa, M. A. J. Am. Chem. Soc. 1993, 115, 7166-7172. (e) Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. J. Am. Chem. Soc. 1995, 117, 3448-3467.
27. For reviews on polyether antibiotics see: (a) Polyether Antibiotics: Naturally Occurring Acid Ionophores; Westley, J. W., Ed.; Marcel Dekker: New York, 1982; Vols. 1 and 2. (b) Wierenga, W. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley: New York, 1992; Vol. 4, pp 263-351. For recent syntheses see: (c) Ireland, R. E.; Armstrong, J. D., III.; Leberton, J.; Meissner, R. S.; Rizzacasa, M. A. J. Am. Chem. Soc. 1993, 115, 7152-7156. (d) Ireland, R. E.; Meissner, R. S.; Rizzacasa, M. A. J. Am. Chem. Soc. 1993, 115, 7166-7172. (e) Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. J. Am. Chem. Soc. 1995, 117, 3448-3467.
28. For reviews on polyether antibiotics see: (a) Polyether Antibiotics: Naturally Occurring Acid Ionophores; Westley, J. W., Ed.; Marcel Dekker: New York, 1982; Vols. 1 and 2. (b) Wierenga, W. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley: New York, 1992; Vol. 4, pp 263-351. For recent syntheses see: (c) Ireland, R. E.; Armstrong, J. D., III.; Leberton, J.; Meissner, R. S.; Rizzacasa, M. A. J. Am. Chem. Soc. 1993, 115, 7152-7156. (d) Ireland, R. E.; Meissner, R. S.; Rizzacasa, M. A. J. Am. Chem. Soc. 1993, 115, 7166-7172. (e) Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. J. Am. Chem. Soc. 1995, 117, 3448-3467.
29. (a) Pettit, G. R.; Albert, A. H.; Brown, P. J. Am. Chem. Soc. 1972, 94, 8095-8099.
30. (b) Oikawa, M.; Oikawa, H.; Ichihara, A. Tetrahedron Lett. 1993, 34, 4797-4800.
31. (c) Oikawa, H.; Oikawa, M.; Ichihara, A.; Kobayashi, K.; Uramoto, M. Tetrahedron Lett. 1993, 34, 5303-5306.
32. (d) Zhao, Y.-b.; Albizati, K. F. Tetrahedron Lett. 1993, 34, 575-578.
33. (e) Oikawa, M.; Oikawa, H.; Ichihara, A. Tetrahedron 1995, 51, 6237-6254.
34. (f) Kotsuki, H. Synlett 1992, 97-106.
35. Part of this work was published previously as a preliminary communication: Dorta, R. L.; Freire, R.; Martín, A.; Súarez, E.; Prangé, T. Tetrahedron Lett. 1995, 36, 7309-7312.
36. (a) Agrawal, P. K.; Jain, D. C.; Gupta, R. K.; Thakur, R. S. Phytochemistry 1985, 24, 2479-2496.
37. (b) Mahano, S. B.; Ganguly, A. N.; Sahu, N. P. Phytochemistry 1982, 21, 959-978.
38. (c) Tschesche, V. R.; Wulf, G. Prog. Chem. Org. Nat. Prod. 1973, 30, 461-606.
39. (a) Barton, D. H. R.; Sammes, P. G.; Taylor, M. V.; Werstiuk, E. J. Chem Soc. C 1970, 1977-1981.
40. (b) Gonzalez, A. G.; Freire, R.; García-Estrada, M. G.; Salazar, J. A.; Suárez, E. Tetrahedron 1972, 28, 1289-1297.
41. (c) Gonzalez, A. G.; Freire, R.; García-Estrada, M. G.; Salazar, J. A.; Suárez, E. Anal. Chim. 1971, 67, 903-905.
42. The author has deposited the atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, upon request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
43. Garegg, P. J.; Samuelsson, B. J. Chem. Soc., Perkin Trans. 1 1980, 2866-2869.
44. Hernández, R.; Marrero-Tellado, J. J.; Prout, K.; Suárez, E. J. Chem. Soc., Chem. Commun. 1992, 275-277.
45. MMX force field as implemented in PCMODEL (v. 4.0), Serena Software, Bloomington IN, 47402-3076.
46. (a) Ishihara, K.; Mori, A.; Yamamoto, H. Tetrahedron 1990, 46, 4595-4612.
47. (b) Ishihara, K.; Hanaki, N.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 7040-7075.
48. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: New York, 1988.