An efficient and stereoselective synthesis of 9-cis-retinoic acid

Journal of Organic Chemistry

Volumn 61, Issue 10, 1996, Pages 3542-3544

  Bennani, Youssef L ^a  

^a LIGAND PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RETINOIC ACID;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029951985     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952189g     Document Type: Article

References (30)

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16. For the preparation of the corresponding carboxylic acid analogue of nitrile 6, through a lactone intermediate, see: (c) Cainelli, G.; Cardillo, G.; Orena, M. J. Chem. Soc., Perkin Trans. 1 1979, 1597. (d) Dugger, R. W.; Heathcock, C. H. J. Org. Chem. 1980, 45, 1181. For the preparation of aldehyde 7 through a lactol intermediate, see ref 7a,b and: (e) Bennani, Y. L.; Boehm, M. F. J. Org. Chem. 1995, 60, 1195.
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23. 1H-NMR.
24. For 1,4-addition to acetylene esters: (a) Corey, E. J.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 1851. (b) Ernst, L.; Hopf, H.; Krause, N. J. Org. Chem. 1987, 52, 398. For 1,4-addition to acetylenic nitriles: (c) Westmijze, H.; Vermeer, P. Westmijze, H., Kleijn, H., Vermeer, P. Tetrahedron Lett. 1979, 3327; Synthesis 1978, 454 and references cited therein. For the preparation of a mixture of nitriles: (d) Cainelli, G.; Cardillo, G.; Contento, M.; Grasselli, P. Umani Ronchi A. Gazz. Chim. Ital. 1973, 103, 117. (e) Andriamialisoa, Z.; Valla, A.; Zennache, S.; Giraud, M.; Potier, P. Tetrahedron Lett. 1993, 34, 8091.
25. For 1,4-addition to acetylene esters: (a) Corey, E. J.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 1851. (b) Ernst, L.; Hopf, H.; Krause, N. J. Org. Chem. 1987, 52, 398. For 1,4-addition to acetylenic nitriles: (c) Westmijze, H.; Vermeer, P. Westmijze, H., Kleijn, H., Vermeer, P. Tetrahedron Lett. 1979, 3327; Synthesis 1978, 454 and references cited therein. For the preparation of a mixture of nitriles: (d) Cainelli, G.; Cardillo, G.; Contento, M.; Grasselli, P. Umani Ronchi A. Gazz. Chim. Ital. 1973, 103, 117. (e) Andriamialisoa, Z.; Valla, A.; Zennache, S.; Giraud, M.; Potier, P. Tetrahedron Lett. 1993, 34, 8091.
26. For 1,4-addition to acetylene esters: (a) Corey, E. J.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 1851. (b) Ernst, L.; Hopf, H.; Krause, N. J. Org. Chem. 1987, 52, 398. For 1,4-addition to acetylenic nitriles: (c) Westmijze, H.; Vermeer, P. Westmijze, H., Kleijn, H., Vermeer, P. Tetrahedron Lett. 1979, 3327; Synthesis 1978, 454 and references cited therein. For the preparation of a mixture of nitriles: (d) Cainelli, G.; Cardillo, G.; Contento, M.; Grasselli, P. Umani Ronchi A. Gazz. Chim. Ital. 1973, 103, 117. (e) Andriamialisoa, Z.; Valla, A.; Zennache, S.; Giraud, M.; Potier, P. Tetrahedron Lett. 1993, 34, 8091.
27. For 1,4-addition to acetylene esters: (a) Corey, E. J.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 1851. (b) Ernst, L.; Hopf, H.; Krause, N. J. Org. Chem. 1987, 52, 398. For 1,4-addition to acetylenic nitriles: (c) Westmijze, H.; Vermeer, P. Westmijze, H., Kleijn, H., Vermeer, P. Tetrahedron Lett. 1979, 3327; Synthesis 1978, 454 and references cited therein. For the preparation of a mixture of nitriles: (d) Cainelli, G.; Cardillo, G.; Contento, M.; Grasselli, P. Umani Ronchi A. Gazz. Chim. Ital. 1973, 103, 117. (e) Andriamialisoa, Z.; Valla, A.; Zennache, S.; Giraud, M.; Potier, P. Tetrahedron Lett. 1993, 34, 8091.
28. For 1,4-addition to acetylene esters: (a) Corey, E. J.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 1851. (b) Ernst, L.; Hopf, H.; Krause, N. J. Org. Chem. 1987, 52, 398. For 1,4-addition to acetylenic nitriles: (c) Westmijze, H.; Vermeer, P. Westmijze, H., Kleijn, H., Vermeer, P. Tetrahedron Lett. 1979, 3327; Synthesis 1978, 454 and references cited therein. For the preparation of a mixture of nitriles: (d) Cainelli, G.; Cardillo, G.; Contento, M.; Grasselli, P. Umani Ronchi A. Gazz. Chim. Ital. 1973, 103, 117. (e) Andriamialisoa, Z.; Valla, A.; Zennache, S.; Giraud, M.; Potier, P. Tetrahedron Lett. 1993, 34, 8091.
29. For 1,4-addition to acetylene esters: (a) Corey, E. J.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 1851. (b) Ernst, L.; Hopf, H.; Krause, N. J. Org. Chem. 1987, 52, 398. For 1,4-addition to acetylenic nitriles: (c) Westmijze, H.; Vermeer, P. Westmijze, H., Kleijn, H., Vermeer, P. Tetrahedron Lett. 1979, 3327; Synthesis 1978, 454 and references cited therein. For the preparation of a mixture of nitriles: (d) Cainelli, G.; Cardillo, G.; Contento, M.; Grasselli, P. Umani Ronchi A. Gazz. Chim. Ital. 1973, 103, 117. (e) Andriamialisoa, Z.; Valla, A.; Zennache, S.; Giraud, M.; Potier, P. Tetrahedron Lett. 1993, 34, 8091.
30. Ratios vary between 10:1 to 15:1 on different runs and concentrations.