Formal total synthesis of (±)-aflatoxin B2 utilizing the rhodium carbenoid dipolar cycloaddition

Tetrahedron Letters

Volumn 37, Issue 14, 1996, Pages 2391-2394

  Pirrung, Michael C ^a   Lee, Yong Rok ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

Baeyer Villiger; cycloaddition; diazocompound; rhodium acetate; total synthesis

Indexed keywords

AFLATOXIN B2;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029866375     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00412-1     Document Type: Article

References (33)

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7. Castellino, A. J.; Rapoport, H. J. Org. Chem. 1986, 51, 1006-1011. Sloan, C. P.; Cuevas, J. C.; Quesnelle, C.; Snieckus, V. Tetrahedron Lett. 1988, 29, 4685-4686. Wolff, S.; Hoffmann, H. M. R. Synthesis 1988, 760-761. Weeratunga, G.; Horne, S.; Rodrigo, R. J. Chem. Soc., Chem. Commun. 1988, 721-722. Horne, S.; Weeratunga, G.; Rodrigo, R. J. Chem. Soc., Chem. Commun. 1990, 39-41. Kraus, G. A.; Johnston B. E.; Applegate, J. M. J. Org. Chem. 1991, 56, 5688-5691. Koreeda, M.; Dixon, L. A.; Hsi, J. D. Synlett, 1993, 555-556. Civitello, E. R.; Rapoport, H. J. Org. Chem. 1994, 59, 3775-3782.
8. Castellino, A. J.; Rapoport, H. J. Org. Chem. 1986, 51, 1006-1011. Sloan, C. P.; Cuevas, J. C.; Quesnelle, C.; Snieckus, V. Tetrahedron Lett. 1988, 29, 4685-4686. Wolff, S.; Hoffmann, H. M. R. Synthesis 1988, 760-761. Weeratunga, G.; Horne, S.; Rodrigo, R. J. Chem. Soc., Chem. Commun. 1988, 721-722. Horne, S.; Weeratunga, G.; Rodrigo, R. J. Chem. Soc., Chem. Commun. 1990, 39-41. Kraus, G. A.; Johnston B. E.; Applegate, J. M. J. Org. Chem. 1991, 56, 5688-5691. Koreeda, M.; Dixon, L. A.; Hsi, J. D. Synlett, 1993, 555-556. Civitello, E. R.; Rapoport, H. J. Org. Chem. 1994, 59, 3775-3782.
9. Castellino, A. J.; Rapoport, H. J. Org. Chem. 1986, 51, 1006-1011. Sloan, C. P.; Cuevas, J. C.; Quesnelle, C.; Snieckus, V. Tetrahedron Lett. 1988, 29, 4685-4686. Wolff, S.; Hoffmann, H. M. R. Synthesis 1988, 760-761. Weeratunga, G.; Horne, S.; Rodrigo, R. J. Chem. Soc., Chem. Commun. 1988, 721-722. Horne, S.; Weeratunga, G.; Rodrigo, R. J. Chem. Soc., Chem. Commun. 1990, 39-41. Kraus, G. A.; Johnston B. E.; Applegate, J. M. J. Org. Chem. 1991, 56, 5688-5691. Koreeda, M.; Dixon, L. A.; Hsi, J. D. Synlett, 1993, 555-556. Civitello, E. R.; Rapoport, H. J. Org. Chem. 1994, 59, 3775-3782.
10. Castellino, A. J.; Rapoport, H. J. Org. Chem. 1986, 51, 1006-1011. Sloan, C. P.; Cuevas, J. C.; Quesnelle, C.; Snieckus, V. Tetrahedron Lett. 1988, 29, 4685-4686. Wolff, S.; Hoffmann, H. M. R. Synthesis 1988, 760-761. Weeratunga, G.; Horne, S.; Rodrigo, R. J. Chem. Soc., Chem. Commun. 1988, 721-722. Horne, S.; Weeratunga, G.; Rodrigo, R. J. Chem. Soc., Chem. Commun. 1990, 39-41. Kraus, G. A.; Johnston B. E.; Applegate, J. M. J. Org. Chem. 1991, 56, 5688-5691. Koreeda, M.; Dixon, L. A.; Hsi, J. D. Synlett, 1993, 555-556. Civitello, E. R.; Rapoport, H. J. Org. Chem. 1994, 59, 3775-3782.
11. Castellino, A. J.; Rapoport, H. J. Org. Chem. 1986, 51, 1006-1011. Sloan, C. P.; Cuevas, J. C.; Quesnelle, C.; Snieckus, V. Tetrahedron Lett. 1988, 29, 4685-4686. Wolff, S.; Hoffmann, H. M. R. Synthesis 1988, 760-761. Weeratunga, G.; Horne, S.; Rodrigo, R. J. Chem. Soc., Chem. Commun. 1988, 721-722. Horne, S.; Weeratunga, G.; Rodrigo, R. J. Chem. Soc., Chem. Commun. 1990, 39-41. Kraus, G. A.; Johnston B. E.; Applegate, J. M. J. Org. Chem. 1991, 56, 5688-5691. Koreeda, M.; Dixon, L. A.; Hsi, J. D. Synlett, 1993, 555-556. Civitello, E. R.; Rapoport, H. J. Org. Chem. 1994, 59, 3775-3782.
12. Pirrung, M.C.; Zhang, J.; McPhail, A.T. J. Org. Chem., 1991, 56, 6269-6271. Pirrung, M. C.; Zhang, J. Tetrahedron Lett. 1992, 33, 5987-5990. Pirrung, M. C.; Lee, Y.R. Tetrahedron Lett. 1994, 35, 6231. Pirrung, M. C.; Zhang, J.; Morehead, Jr., A. T. Tetrahedron Lett. 1994, 35, 6229. Lee, Y.R.; Morehead, Jr., A. T. Tetrahedron 1995, 51, 4909. Lee, Y.R. Tetrahedron 1995, 51, 3087. Pirrung, M. C.; Zhang, J.; Lackey, K.; Sternbach, D. D.; Brown, F. J. Org. Chem., 1995, 60, 2112.
13. Pirrung, M.C.; Zhang, J.; McPhail, A.T. J. Org. Chem., 1991, 56, 6269-6271. Pirrung, M. C.; Zhang, J. Tetrahedron Lett. 1992, 33, 5987-5990. Pirrung, M. C.; Lee, Y.R. Tetrahedron Lett. 1994, 35, 6231. Pirrung, M. C.; Zhang, J.; Morehead, Jr., A. T. Tetrahedron Lett. 1994, 35, 6229. Lee, Y.R.; Morehead, Jr., A. T. Tetrahedron 1995, 51, 4909. Lee, Y.R. Tetrahedron 1995, 51, 3087. Pirrung, M. C.; Zhang, J.; Lackey, K.; Sternbach, D. D.; Brown, F. J. Org. Chem., 1995, 60, 2112.
14. Pirrung, M.C.; Zhang, J.; McPhail, A.T. J. Org. Chem., 1991, 56, 6269-6271. Pirrung, M. C.; Zhang, J. Tetrahedron Lett. 1992, 33, 5987-5990. Pirrung, M. C.; Lee, Y.R. Tetrahedron Lett. 1994, 35, 6231. Pirrung, M. C.; Zhang, J.; Morehead, Jr., A. T. Tetrahedron Lett. 1994, 35, 6229. Lee, Y.R.; Morehead, Jr., A. T. Tetrahedron 1995, 51, 4909. Lee, Y.R. Tetrahedron 1995, 51, 3087. Pirrung, M. C.; Zhang, J.; Lackey, K.; Sternbach, D. D.; Brown, F. J. Org. Chem., 1995, 60, 2112.
15. Pirrung, M.C.; Zhang, J.; McPhail, A.T. J. Org. Chem., 1991, 56, 6269-6271. Pirrung, M. C.; Zhang, J. Tetrahedron Lett. 1992, 33, 5987-5990. Pirrung, M. C.; Lee, Y.R. Tetrahedron Lett. 1994, 35, 6231. Pirrung, M. C.; Zhang, J.; Morehead, Jr., A. T. Tetrahedron Lett. 1994, 35, 6229. Lee, Y.R.; Morehead, Jr., A. T. Tetrahedron 1995, 51, 4909. Lee, Y.R. Tetrahedron 1995, 51, 3087. Pirrung, M. C.; Zhang, J.; Lackey, K.; Sternbach, D. D.; Brown, F. J. Org. Chem., 1995, 60, 2112.
16. Pirrung, M.C.; Zhang, J.; McPhail, A.T. J. Org. Chem., 1991, 56, 6269-6271. Pirrung, M. C.; Zhang, J. Tetrahedron Lett. 1992, 33, 5987-5990. Pirrung, M. C.; Lee, Y.R. Tetrahedron Lett. 1994, 35, 6231. Pirrung, M. C.; Zhang, J.; Morehead, Jr., A. T. Tetrahedron Lett. 1994, 35, 6229. Lee, Y.R.; Morehead, Jr., A. T. Tetrahedron 1995, 51, 4909. Lee, Y.R. Tetrahedron 1995, 51, 3087. Pirrung, M. C.; Zhang, J.; Lackey, K.; Sternbach, D. D.; Brown, F. J. Org. Chem., 1995, 60, 2112.
17. Pirrung, M.C.; Zhang, J.; McPhail, A.T. J. Org. Chem., 1991, 56, 6269-6271. Pirrung, M. C.; Zhang, J. Tetrahedron Lett. 1992, 33, 5987-5990. Pirrung, M. C.; Lee, Y.R. Tetrahedron Lett. 1994, 35, 6231. Pirrung, M. C.; Zhang, J.; Morehead, Jr., A. T. Tetrahedron Lett. 1994, 35, 6229. Lee, Y.R.; Morehead, Jr., A. T. Tetrahedron 1995, 51, 4909. Lee, Y.R. Tetrahedron 1995, 51, 3087. Pirrung, M. C.; Zhang, J.; Lackey, K.; Sternbach, D. D.; Brown, F. J. Org. Chem., 1995, 60, 2112.
18. Pirrung, M.C.; Zhang, J.; McPhail, A.T. J. Org. Chem., 1991, 56, 6269-6271. Pirrung, M. C.; Zhang, J. Tetrahedron Lett. 1992, 33, 5987-5990. Pirrung, M. C.; Lee, Y.R. Tetrahedron Lett. 1994, 35, 6231. Pirrung, M. C.; Zhang, J.; Morehead, Jr., A. T. Tetrahedron Lett. 1994, 35, 6229. Lee, Y.R.; Morehead, Jr., A. T. Tetrahedron 1995, 51, 4909. Lee, Y.R. Tetrahedron 1995, 51, 3087. Pirrung, M. C.; Zhang, J.; Lackey, K.; Sternbach, D. D.; Brown, F. J. Org. Chem., 1995, 60, 2112.
19. Pirrung, M. C.; Lee, Y. R. J. Chem. Soc., Chem. Commun. 1995, 673.
20. 2: C, 48.98; H, 4.11. Found: C, 48.95; H, 4.15.
21. 5: C, 60.49; H, 5.92. Found: C, 60.10; H, 5.97.
22. 3): δ 2.23-2.31 (m, 2H), 3.67 (m, 1H), 4.07-4.17 (m, 2H), 6.41 (d, J = 5.7 Hz, 1H), 6.62 (s, 1H), 6.90 (s, 1H), 6.97 (s, 1H), 9.82 (s, 1H, CHO).
23. 5: C, 61.02; H, 5.12. Found: C, 60.89; H, 5.15.
24. 5Si: 336.1393. Found: 336.1392.
25. Krow, G. R. Org. React. (N. Y.) 1993, 43, 251-798. Iinuma, M.; Tanaka, T.; Matsuura, S. Heterocycles 1983, 20, 2425. Syper, L. Synthesis, 1989, 167-72.
26. Krow, G. R. Org. React. (N. Y.) 1993, 43, 251-798. Iinuma, M.; Tanaka, T.; Matsuura, S. Heterocycles 1983, 20, 2425. Syper, L. Synthesis, 1989, 167-72.
27. Krow, G. R. Org. React. (N. Y.) 1993, 43, 251-798. Iinuma, M.; Tanaka, T.; Matsuura, S. Heterocycles 1983, 20, 2425. Syper, L. Synthesis, 1989, 167-72.
28. Godfrey, I. M.; Sargent, M. V.; Elix, J. A. J. Chem. Soc., Perkin Trans. 1, 1974, 1353.
29. 3): δ 0.20 (s, 3H), 0.25 (s, 3H), 1.02 (s, 9H), 2.22-2.27 (m, 2H), 3.63-3.68 (m, 1H), 3.99 (m, 1H), 4.11 (m, 1H), 6.37 (d, J = 5.7 Hz, 1H), 6.14 (s, 1H), 6.22 (s, 1H), 8.23 (s, 1H, OH).
30. 5Si: 324.1395. Found: 324.1406.
31. Camps, F.; Coll, J.; Messeguer, A.; Pericas, M. A. Tetrahedron Lett. 1981, 22, 3895-3896.
32. -1.
33. 3): δ 2.12-2.20 (m, 2H), 3.63-3.71 (m, 1H), 3.73 (s, 3H), 3.72-3.79 (m, 2H), 3.99 (m, 1H), 4.09 (m, 1H), 4.80 (br s, 1H, OH), 5.90 (d, J = 2.0 Hz, 1H), 6.04 (d, J = 2.0 Hz, 1H), 6.32 (d, J = 5.6 Hz, 1H).