A convenient synthesis of dengibsin

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3920-3922

  Jones Jr , Winton D ^a   Ciske, Fred L ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DENGIBSIN; FLUORENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029898902     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9601369     Document Type: Article

References (18)

1. (a) Talapatra, S. K.; Bose, S.; Malik, A. K.; Talapatra, B. Tetrahedron 1985, 41, 2765-2769.
2. (b) Talapatra, S. K.; Chakraborty, S.; Bose, S.; Talapatra, B. Ind. J. Chem. 1988, 27B, 250-252.
3. (a) Sargent, M. V. J. Chem Soc., Perkin Trans. 1 1987, 2553-2563. (b) To the best of our knowledge, compound 1b has not been previously reported.
4. (a) Wang, W.; Snieckus, V. J. Org. Chem. 1992, 57, 424-426.
5. (b) Fu, J.-M.; Zhao, B.-P.; Sharp, M. J.; Snieckus, V. Can. J. Chem. 1994, 72, 227-236.
6. 2
7. Gant, T. A.; Meyers, A. I. Tetrahedron 1994, 50, 2297-2360.
8. Bos, M. E.; Wulff, W. D.; Miller, R. A.; Chamberlin, S.; Brandvold, T. A. J. Am. Chem Soc. 1991, 113, 9293-9319.
9. (a) The published procedure of Sargent (ref 2) was modified (see the Experimental Section).
10. (b) Dodd, J. H.; Guan, J.; Schwender C. F. Synth. Commun. 1993, 23, 1003-1008.
11. (a) Coste, J.; Le- Nguyen, D.; Castro, B. Tetrahedron Lett. 1990, 31, 205-208.
12. (b) Frerot, E.; Coste, J.; Pantaloni, A.; Dufour, M.-N.; Jouin, P. Tetrahedron. 1991, 47, 259-270.
13. PyBOP has the structure shown below and can be purchased from Nova Biochem, San Diego, CA. (Formula Presented)
14. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
15. (a) A number of these compounds may exist as mixtures of atropisomers.
16. (b) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977-991.
17. Meyers, A. I.; Slade, J. J. Org. Chem. 1980, 45, 2785-2791.
18. In a later experiment, 2.03 g of 7 was converted into 1.40 g of dengibsin 13.