Unusual reductive cleavage of 7-oxa-bicyclo[2,2,1]heptane system for the synthesis of tetrahydrofuran derivatives

Tetrahedron

Volumn 53, Issue 25, 1997, Pages 8519-8530

  Viti, Giovanni ^a   Perrotta, Enzo ^a   Giannotti, Danilo ^a   Nannicini, Rossano ^a  

^a Menarini Ricerche SpA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030908604     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00510-3     Document Type: Article

References (19)

1. (a) Sheha, M. M.; Nakata, S.; Enomoto, H.; Kimura, T.; Mimoto, T.; Hattori, N.; Mahfouz, N. M.; Hassan, H. Y.; Youssel, A. F.; et al. Pept. Chem. 1995, 32, 349-352.
2. (b) Kohn, H.; Sawhney, K. N.; Bardel, P.; Robertson, D. W.; Leander, J. D. J. Med. Chem. 1993, 36, 3350-3360.
3. (c) Januṡz, J. M.; Young, P. A.; Blum, R. B.; Riley, C. M. J. Med. Chem. 1990, 33, 1676-1682.
4. (d) Williams, R. M.; Sinclair, P. J.; Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547-57.
5. (e) Ben-Ishai, D.; Sataty, I.; Bernstein, Z. Tetrahedron, 1976, 32, 1571-1573.
6. (f) Katagiri, K.; Tori, K.; Kimura, Y.; Yoshida, T.; Nagasaki, T.; Minato, H. J. Med. Chem. 1967, 10, 1149-1154.
7. Zefirov, N.S.; Ivanova, R. A.; Filatova, R. S.; Yur'ev, Y. K. J. Gen. Chem. USSR 1965, 35, 1794-1797.
8. 3 in the ethereal solution of exo-cis-7-oxabicyclo[2,2,1]heptane-2,3-dicarboxylic acid anhydride, collecting the solid by filtration, pouring it into water, treating, while cooling, with hydrochloric acid until pH 3 and using the collected solid material , still wet and without any purification, immediately in the Hofmann reaction.
9. (a) Carey, F. A.; Tremper, H. S. J. Org. Chem. 1971, 36, 758-761
10. (b) Carey, F. A.; Tremper, H. S. J. Am. Chem. Soc. 1968, 90, 2578-2586.
11. Dehydratation of 3a to the oxazine 4a was easily achieved, in a shorter reaction time, with the more powerful dehydrating agent thionyl chloride.
12. (a) Mc Clure, D. E.; Arison, B. H.; Jones, J. H.; Baldwin, J. J. J. Org. Chem. 1981, 46, 2431-2433
13. (b) Maryanoff, B. E.; Almond Jr., H. R. J. Org. Chem. 1986, 51, 3295-3302.
14. 2 on the hydrochloric salt of 6b.
15. Carlsen, P.H.J.; Katsuki V.S.M.; Sharpless, K.B. J. Org. Chem. 1981, 46, 3936-3938.
16. 2) 25.4, 28.9, 80.0, (CH) 61.4, 69.0, 127.2 (2C), 128.7 (2C), 131.9, 199.6 (C) 134.1, 169.4 .
17. G. Balacco , J. Chem. Inf. Comput. Sci., 1994, 34, 1235-1241.
18. (a) Hagishita, S. ; Seno, K. Chem. Pharm. Bull. 1989, 37, 327-335.
19. (b) Eggelte, T. A.; deKonig, H.; Huisman, H. O. Tetrahedron 1973, 29, 2445-2491