Substituted 1,7-dioxabicyclo[3.3.0]octanes: New easy access to the perhydrofurofuran core of aflatoxins and analogues

Tetrahedron Letters

Volumn 38, Issue 12, 1997, Pages 2187-2190

  Alonso, Francisco ^a   Lorenzo, Emilio ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AFLATOXIN; FURAN DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; HYDROLYSIS; REACTION ANALYSIS;

EID: 0031585040     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00278-5     Document Type: Article

References (33)

1. 1. For a review, see: Schuda, P. Top. Curr. Chem. 1980, 91, 75-111.
2. 2. For leading references, see: (a) Knight, J. A.; Roberts, J. C.; Roffey, P.; Sheppard, A. H. J. Chem. Soc., Chem. Commun. 1966, 706-707.
3. (b) Büchi, G.; Foulkes, D. M.; Kuromo, M.; Mitchell, G. F.; Schneider, R. S. J. Am. Chem. Soc. 1967, 89, 6745-6753.
4. (c) Büchi, G.; Francisco, M. A.; Lusch, J. M.; Schuda, P. F. J. Am. Chem. Soc. 1981, 103, 3497-3501.
5. (d) Castellina, A. J.; Rapoport, H. J. Org. Chem. 1986, 51, 1006-1011.
6. (e) Weeratunga, G.; Horne, S.; Rodrigo, R. J. Chem. Soc., Chem. Commun. 1988, 721-722.
7. (f) Wolf, S.; Hoffmann, H. M. R. Synthesis 1988, 760-763.
8. (g) Horne, S.; Weeratunga, G.; Rodrigo, R. J. Chem. Soc., Chem. Commun. 1990, 39-41.
9. (h) Kraus, G. A.; Johnston, B. E.; Applegate, J. M. J. Org. Chem. 1991, 56, 5688-5691.
10. (i) Koreeda, M.; Dixon, L. A.; Hsi, J. D. Synlett 1993, 555-556.
11. (j) Civitello, E. R.; Rapoport, H. J. Org. Chem. 1994, 59, 3775-3782.
12. (k) Pirrung, M. C.; Lee, Y. R. Tetrahedron Lett. 1996, 37, 2391-2394.
13. 3. Busby, W. F., Jr.; Wogan, G. N. In Chemical Carcinogens, 2nd ed.; Searle, C., Ed.; American Chemical Society: Washington, DC, 1984; Vol. 182, pp 945-1136.
14. 4. Mycotoxins-Economic and Health Risks, Council for Agricultural Science and Technology: Ames, 1988 (taken from reference 2h).
15. 5. See, for instance: (a) Mulzer, J.; Mohr, J.-T. J. Org. Chem. 1994, 59, 1160-1165.
16. (b) Raman, J. V.; Lee, H. K.; Vleggaar, R.; Cha, J. K. Tetrahedron Lett. 1995, 36, 3095-3098.
17. 6. Ghosh, A. K.; Kincaid, J. F.; Walters, D. E.; Chen. Y.; Chaudhuri, N. C.; Thompson, W. J.; Culberson, C.; Fitzgerald, P. M. D.; Lee, H. Y.; McKee, S. P.; Munson P. M.; Duong, T. T.; Darke, P. L.; Zugay, J. A.; Schleif, W. A.; Axel, M. G.; Lin, J.; Huff, J. R. J. Med. Chem. 1996, 39, 3278-3290, and references cited therein.
18. 7. See, for instance: Chen, H.; Tan, R. X.; Liu, Z.; Zhang, Y. J. Nat. Prod. 1996, 59, 668-670, and references cited therein.
19. 8. (a) For the first paper on this methodology, see: Yus, M.; Ramón, D. J. J. Chem. Soc., Chem. Commun. 1991, 398-400.
20. (b) For a recent review, see: Yus, M. Chem. Soc. Rev. 1996, 155-161.
21. 9. For the last paper on this topic from our laboratory, see: Alonso, E.; Ramón, D. J.; Yus, M. Tetrahedron 1996, 52, 14341-14348.
22. 10. (a) For a review, see: Nájera, C.; Yus, M. Trends Org. Chem. 1991, 2, 155-181.
23. (b) For the last paper on this topic from our laboratory, see: Ramón, D. J.; Yus, M. Tetrahedron 1996, 52, 13739-13750.
24. 11. For the last paper on this topic from our laboratory, see: Guijarro, A.; Yus, M. Tetrahedron 1996, 52, 1797-1810.
25. 12. This compound, which is commercially available (Aldrich), can be easily prepared from pentaerythritol: Mondanaro-Lynch, K.; Dailey, W. P. J. Org. Chem. 1995, 60, 4666-4668.
26. 13. For a monograph on this process, see: Blomberg, C. The Barbier Reaction and Related One-Pot Processes; Springer-Verlag: Berlin, 1993.
27. 14. (a) Ramón, D. J.; Yus, M. Tetrahedron Lett. 1992, 33, 2217-2220.
28. (b) Gómez, C.; Ramón, D. J.; Yus, M. Tetrahedron 1993, 49, 4117-4126.
29. 15. See, for instance: Zweifel, G.; Brown, H. C. Org. React. 1963, 13, 1-54.
30. 16. Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 2647-2650.
31. 17. Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1974, 3221-3224.
32. column = 60°C (3 min) and 60-270C (15°C/min).
33. 19. The obtained nOe values for cisII-3b are as follows: (equation presented)