Convergent and Efficient Palladium-Effected Synthesis of 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid (DDATHF)

Journal of Organic Chemistry

Volumn 54, Issue 15, 1989, Pages 3618-3624

  Taylor, Edward C ^a   Wong, George S K ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LOMETREXOL;

DRUG SYNTHESIS; METHODOLOGY; NONHUMAN;

EID: 0024358248     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00276a023     Document Type: Article

References (17)

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4. Beardsley, G. P.; Taylor, E. C.; Grindey, G. B.; Moran, R. G. In Chemistry and Biology of Pteridines; Cooper, B. A., Whitehead, V. M., Eds.; Walter de Gruvter: Berlin, 1986; P 953.
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9. Taylor, E. C.; Hamby, J. M.; Shih, C.; Grindey, G. B.; Rinzel, S. M.; Beardsley, G. P.: Moran. R. G. J. Med. Chem., in Dress.
10. Shih, C.; Grindey, G. B.; Houghton, P. J.; Houghton, J. A. Proc. Am. Assoc. Cancer Res. 1988, 29, 283.
11. Two further syntheses of DDATHF have recently been described that constitute modifications of our originally described Wittig strategy; these involve condensation of 2-acetyl-6-formyl-5-deazapterin or of 6-formyl-2,4-diamino-5-deazapteridine with the Wittig reagents derived from diethyl [4-(bromomethyl)benzoyl]glutamate or methyl 4-(bromomethyl)benzoate, respectively (Boschelli, D. H.; Webber, S.; Whiteley, J. M.; Oronsky, A. L.; Kerwar, S. S. Arch. Biochem. Biophys. 1988, 265, 43. Piper, J. R.; McCaleb, G. S.; Montgomery, J. A.; Kisliuk, R. L.; Gaumont, Y.; Thorndike, J.; Sirotnak, F. M. J. Med. Chem. 1988, 31, 2164). We have also recently described a Diels-Alder route to DDATHF (Taylor, E. C.: Harrington, P. M.: Warner. J. C. Heterocycles 1988. 27. 1925).
12. Setliff, F. L.; Hule, W. R. J. Chem. Eng. Data 1981, 26, 332.
13. For representative examples of palladium-catalyzed CC coupling reactions of halo-substituted pyridines or condensed pyridines, see: (a) Sakamoto, T.; Shiraiwa, M.; Kondo, Y.; Yamanaka, H. Synthesis 1983, 312.
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