Enantiopure N-Acyldihydropyridones as Synthetic Intermediates: Asymmetric Synthesis of (-)-Slaframine

Organic Letters

Volumn 1, Issue 12, 1999, Pages 1941-1943

  Comins, Daniel L ^a   Fulp, Alan B ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; MYCOTOXIN; PYRIDONE DERIVATIVE; SLAFRAMINE;

ARTICLE; CHEMISTRY; HYPHOMYCETES; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; MYCOTOXINS; PYRIDONES; RHIZOCTONIA; STEREOISOMERISM;

EID: 0033576430     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991083v     Document Type: Article

References (27)

1. (a) Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis; Wiley: New York, 1987.
2. (b) Ager, D. J.; East, M. B. Asymmetric Synthetic Methodology; CRC Press: New York, 1995.
3. Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J. J. Am. Chem. Soc. 1999, 121, 2651 and references therein.
4. Harris, C. M.; Schneider, M. J.; Ungemach, F. S.; Hill, J. E.; Harris, T. M. J. Am. Chem. Soc. 1988, 110, 940 and references therein.
5. For a review, see: Croom, W. J.; Hagler, W. M.; Froetschel, M. A.; Johnson, A. D. J. Anim. Sci. 1995, 73, 1499.
6. Aust, S. D. Biochem. Pharmacol. 1969, 18, 929.
7. (a) Sibi, M. P.; Christensen, J. W. J. Org. Chem. 1999, 64, 6434.
8. (b) Knight, D. W.; Sibley, A. W. J. Chem. Soc., Perkin Trans. 1 1997, 2179 and references therein.
9. Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719.
10. (a) Comins, D. L.; Salvador, J. M. J. Org. Chem. 1993, 58, 4656.
11. (b) Both (+)- and (-)-TCC alcohols are available from Aldrich Chemical Co.
12. The yield is of diastereomerically pure 4 isolated by radial preparative layer chromatography. The reaction proceeded in 87% de.
13. (a) Comins, D. L.; Chen, X.; Morgan, L. A. J. Org. Chem. 1997, 62, 7435.
14. (b) Comins, D. L.; Joseph, S. P.; Chen, X. Tetrahedron Lett. 1995, 36, 9141.
15. (a) Comins, D. L.; Dehghani, A.; Foti, C. J.; Joseph, S. P. Org. Synth. 1997, 74, 77.
16. (b) Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299.
17. For other examples of phenylselenocyclocarbamation reactions, see: (a) Berkowitz, D. B.; Pedersen, M. L.; Jahng, W. Tetrahedron Lett. 1996, 37, 4309.
18. (b) Takano, S.; Hatakeyama, S. Heterocycles 1982, 19, 1243.
19. This conversion was carried out on racemic 10. The product 11 exhibited NMR spectra in agreement with literature values, see: Kano, S.; Yokomatsu, T.; Yuasa, Y.; Shibuya, S.; Heterocycles 1986, 24, 621.
20. Kotsuki, H.; Datta, P. K.; Hayakawa, H.; Suenaga, H. Synthesis 1995, 1348.
21. Edwards, D. A.; Richards, R. J. Chem. Soc., Dalton Trans. 1973, 2463. Method g was used to prepare fresh copper(I) acetate.
22. For previous preparations of vinyl acetates from vinyl bromides using copper(I) acetate, see: (a) Klumpp, G. W.; Bos, H.; Schakel, M.; Schmitz, R. F.; Vrielink, J. J. Tetrahedron Lett. 1975, 16, 3429.
23. (b) Lewin, A. H.; Goldberg, N. L. Tetrahedron Lett. 1972, 13, 491.
24. (a) Gensler, W. J.; Hu, M. W. J. Org. Chem. 1973, 38, 3843.
25. (b) Wasserman, H. H.; Vu, C. B. Tetrahedron Lett. 1994, 35, 9779.
26. Pearson, W. H.; Bergmeier, S. C.; Williams, J. P. J. Org. Chem. 1992, 57, 3977.
27. 13C NMR spectra and elemental analysis or high-resolution mass spectra.