Construction of 4-hydroxy-2-pyridinones. Total synthesis of (+)-sambutoxin

Organic Letters

Volumn 2, Issue 20, 2000, Pages 3217-3220

  Williams, David R ^a   Turske, Regis A ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MYCOTOXIN; PYRIDONE DERIVATIVE; SAMBUTOXIN;

ARTICLE; CHEMISTRY; FUSARIUM; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

FUSARIUM; MYCOTOXINS; OXIDATION-REDUCTION; PYRIDONES; STEREOISOMERISM;

EID: 0034609685     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006410+     Document Type: Article

References (39)

1. (a) Kim, J.-C.; Lee, Y.-W. Appl. Environ. Microbiol. 1994, 60, 4380.
2. (b) Kim, J.-C.; Lee, Y.-W.; Tamura, H. T.; Yoshizawa, T. Tetrahedron Lett. 1995, 36, 1047.
3. (a) Ando, K.; Matsuura, I.; Nawata, Y.; Endo, H.; Sasaki, H.; Okytomi, T.; Saehi, T.; Tamura, G. J. Antibiot. 1978, 31, 533.
4. (b) Breinholt, J.; Ludvigsen, S.; Rassing, B. R.; Rosendahl, C. N.; Nielsen, S. E.; Olsen, C. E. J. Nat. Prod. 1997, 60, 33.
5. (c) Alfatafta, A. A.; Gloer, J. B.; Scott, J. A.; Malloch, D. J. Nat. Prod. 1994, 57, 1696.
6. (d) Takahashi, S.; Kakinuma, N.; Uchida, K.; Hashimoto, R.; Yanagisawa, T.; Nakagawa, A. J. Antibiot. 1998, 51, 1051. Fujimoto, H. Ikeda, M.; Yamamoto, K.; Yamazaki, M. J. Nat. Prod. 1993, 56, 1268.
7. (d) Takahashi, S.; Kakinuma, N.; Uchida, K.; Hashimoto, R.; Yanagisawa, T.; Nakagawa, A. J. Antibiot. 1998, 51, 1051. Fujimoto, H. Ikeda, M.; Yamamoto, K.; Yamazaki, M. J. Nat. Prod. 1993, 56, 1268.
8. Williams, D. R.; Sit, S.-Y. J. Org. Chem. 1982, 47, 2846. See also: Rigby, J. H.; Qabar, M. J. J. Org. Chem. 1989, 54, 5852.
9. Williams, D. R.; Sit, S.-Y. J. Org. Chem. 1982, 47, 2846. See also: Rigby, J. H.; Qabar, M. J. J. Org. Chem. 1989, 54, 5852.
10. Williams, D. R.; Bremmer, M. L.; Brown, D. L.; D'Antuono, J. J. Org. Chem. 1985, 50, 2807.
11. Williams, D. R.; Lowder, P. D.; Gu, Y.-G. Tetrahedron Lett. 1997, 38, 327.
12. For an overview of conformational analyses, see: Hoffmann, R. W. Angew. Chem., Int. Ed. 2000, 39, 2054. For a summary of synthesis strategies, see: Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
13. For an overview of conformational analyses, see: Hoffmann, R. W. Angew. Chem., Int. Ed. 2000, 39, 2054. For a summary of synthesis strategies, see: Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
14. Williams, D. R.; Li, J. Tetrahedron Lett. 1994, 35, 5113. In the course of our total synthesis efforts, we prepared and characterized the individual 1,3-syn- and 1,3-anti-diastereomers of the imides below. Distinguishing features can be found in the carbon NMR spectra for chemical shifts of the methyl groups of the asymmetric array as tabulated below. Signals for synisomers were consistently found slightly downfield relative to the corresponding anti-arrangement. (Matrix presented) R = benzyl: δ 16.9 and 19.3 R = benzyl: δ 18.0 and 20.2 R = TBS: δ 16.4 and 19.4 R = TBS: δ 17.6 and 20.5
15. 13C NMR chemical shifts on Boltzmann-weighted MM3 geometries for 1,3-dimethyl arrays has been applied to sambutoxin. Stahl, M.; Schopfer, U.; Frenking, G.; Hoffmann, R. W. J. Org. Chem. 1996, 61, 8083.
16. (a) Nicolas, E.; Russell, K. C.; Hruby, V. J. J. Org. Chem. 1993, 58, 766.
17. (b) Williams, D. R.; Kissel, W. S.; Li, J. Tetrahedron Lett. 1998, 39, 8593, and references therein.
18. 4 reduction, tosylation, and exchange with LiBr in DMF at 50°C (D'Antuono, J. Ph.D. Thesis, Indiana University, 1988. Earley, J. Ph.D. Thesis, Indiana University 1996).
19. Unambiguous confirmation of our 1,3-stereochemistry was established by an independent synthesis using asymmetric allylation methodology to produce the homoallylic alcohol below. See: Roush, W. R.; Palkowitz, A. D.; Palmer, M. A. J. Org. Chem. 1987, 52, 316. Conversion to primary alcohol 7 was accomplished in four steps (65% overall yield). (Matrix presented)
20. For some leading references, see: (a) Wang, Y.-C.; Hung, A.-W.; Chang, C-S.; Yan, T. -H. J. Org. Chem. 1996, 61, 2038.
21. (b) Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747.
22. (c) Braun, M.; Sacha, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1318.
23. (d) Oppolzer, W.; Starkemann, C.; Rodriguez, I.; Bernardinelli, G. Tetrahedron Lett. 1991, 32, 61.
24. 2AlCl led to modest yields (55-65%) of inseparable mixtures of aldol adducts (ratios ∼2:1). Adoption of the Yan procedure (see ref 12a) afforded excellent ≥99:1 anti-diastereoselectivity in our case. However, numerous methods for removal of the auxiliary resulted solely in cleavage of the oxazolidinone ring.
25. (a) Paterson, I.; Wallace, D. J.; Velazquez, S. M. Tetrahedron Lett. 1994, 35, 9083.
26. (b) For a review: Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1.
27. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathchock, C. H. J. Org. Chem. 1991, 56, 2499.
28. (a) Vulpetti, A.; Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron 1993, 49, 685.
29. (b) Myers has described a restricted auxiliary which requires a boat transition state: Myers, A. G.; Widdowson, K. L.; Kukkola, P. J. J. Am. Chem. Soc. 1992, 114, 2765.
30. This is due to conformational preferences in 10 for internal hydrogen bonding. House, H. O.; Crumrine, D. S.; Olmstead, H. D. J. Am. Chem. Soc. 1973, 95, 3310.
31. The availability of the amino aldehyde 14 followed from a route described in our tenellin synthesis (ref 3) using the methyl ester i, N-methylation, Fmoc protection, and adjustment of the oxidation state led to 14 as summarized. (Matrix presented)
32. Williams, D. R.; Lowder, P. D.; Gu, Y.-G.; Brooks, D. A. Tetrahedron Lett. 1997, 38, 331.
33. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
34. Examples of pyridinone methides as reactive intermediates: (a) Asherson, J. L.; Young, D. W. J. Chem. Soc., Chem. Commun. 1977, 916.
35. (b) Girotra, N. N.; Wendler, N. L. Heterocycles 1978, 9, 417.
36. (c) Tietze, L. F.; Brand, S.; Brumby, T.; Fennen, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 665.
37. (d) Snider, B. B.; Lu, Q. J. Org. Chem. 1996, 61, 2839.
38. 3OH).
39. 3OH)) which exhibits significantly different proton NMR data compared to those of the natural metabolite. (Matrix presented)