Expedient Synthesis of a 5α-Steroid Using the Transannular Diels-Alder Strategy

Synlett

Volumn 1996, Issue 11, 1996, Pages 1140-1142

  Couturier, Michel ^a   Deslongchamps, Pierre ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542604373     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5686     Document Type: Article

References (30)

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5. Jung, S. H.; Lee, Y. S.; Park, H.; Kwon, D.-S. Tetrahedron Lett. 1995, 36, 1051; Roush, W. R.; Warmus, J. S.; Works, A. Tetrahedron Lett. 1993, 34, 4427.
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12. Nugent, W. A.; Hobbs, F. W., Jr. Org. Synth. 1988, 66, 52; Nugent, W. A.; Hobbs, F. W., Jr. J. Org. Chem. 1986, 51, 3376; Nugent, W. A.; Hobbs, F. W., Jr. J. Org. Chem. 1983, 48, 5364.
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21. This compound has been previously prepared via a longer procedure. Crévisy, C.; Couturier, M.; Dugave, C.; Dory, Y.L.; Deslongchamps, P. Bull. Soc. Chim. Fr. 1995, 132, 360.
22. Loibner, H.; Zbiral, E. Helv. Chim. Acta 1976, 59, 2100.
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26. 3 was avoided since the enone was found to isomerize via a reversible Michael addition of the phosphine.
27. 8: 446.1941, found: 446.1946.
28. 8: 446.1941; found: 446.1951.
29. 8: 446.1941, found: 446.1946.
30. Drouin, M.; Couturier, M.; Deslongchamps, P. Acta Cryst., (manuscript in preparation).