A short conversion of cyclohexanones to cycloheptenones

Tetrahedron Letters

Volumn 39, Issue 15, 1998, Pages 2097-2098

  Yang, Shangjin ^a   Hungerhoff, Benno ^b   Metz, Peter ^b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEPTENE; CYCLOHEPTENONE; CYCLOHEXANONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0032499095     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00298-6     Document Type: Article

References (17)

1. 1. Heathcock, C. H.; Tice, C. M.; Germroth, T. C. J. Am. Chem. Soc. 1982, 104, 6081-6091.
2. 2. (a) Hoffmann, H. M. R.; Rabe, J. Angew. Chem. 1985, 97, 96-112; Hoffmann, H. M. R.; Rabe, J. Angew. Chem. Int. Ed. Engl. 1985, 24, 94.
3. 2. (a) Hoffmann, H. M. R.; Rabe, J. Angew. Chem. 1985, 97, 96-112; Hoffmann, H. M. R.; Rabe, J. Angew. Chem. Int. Ed. Engl. 1985, 24, 94.
4. (b) Prestwich, G. D. In Natural Product Chemistry; Atta-ur-Rahman, Ed.; Springer-Verlag: Berlin, 1986; pp. 318-329.
5. 3. Metz, P.; Bertels, S.; Fröhlich, R. J. Am. Chem. Soc. 1993, 115, 12595-12596.
6. 4. Hashimoto, N.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1980, 21, 4619-4622.
7. 5. (a) Maruoka, K.; Concepcion, A. B.; Yamamoto, H. J. Org. Chem. 1994, 59, 4725-4726.
8. (b) Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Synthesis 1994, 1283-1290.
9. 6. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011-1013.
10. 7. (a) Ito, Y.; Fujii, S.; Saegusa, T. J. Org. Chem. 1976, 41, 2073-2074.
11. (b) Ito, Y.; Fujii, S.; Nakatsuka, M.; Kawamoto, F.; Saegusa, T. Org. Synth. 1980, 59, 113-122.
12. 2, 20 °C. 1d: Schmid, G.; Hofheinz, W. J. Am. Chem. Soc. 1983, 105, 624-625.
13. 9. All new compounds were completely characterized by appropriate spectroscopic methods and gave satisfactory exact mass molecular weights. The following compounds have been mentioned previously: 4a: Shono,T.; Hayashi, J.; Omoto, H.; Matsumura, Y. Tetrahedron Lett. 1977, 2667-2670. 5a: Ilhyong, R.; Matsumoto, K.; Kameyama, Y.; Ando, M.; Kusumoto, N. J. Am. Chem. Soc. 1993, 115, 12330-12339. 4b: Murphy, R.; Prager, R.; Rolf, H. Aust. J. Chem. 1981, 34, 143-150.
14. 9. All new compounds were completely characterized by appropriate spectroscopic methods and gave satisfactory exact mass molecular weights. The following compounds have been mentioned previously: 4a: Shono,T.; Hayashi, J.; Omoto, H.; Matsumura, Y. Tetrahedron Lett. 1977, 2667-2670. 5a: Ilhyong, R.; Matsumoto, K.; Kameyama, Y.; Ando, M.; Kusumoto, N. J. Am. Chem. Soc. 1993, 115, 12330-12339. 4b: Murphy, R.; Prager, R.; Rolf, H. Aust. J. Chem. 1981, 34, 143-150.
15. 9. All new compounds were completely characterized by appropriate spectroscopic methods and gave satisfactory exact mass molecular weights. The following compounds have been mentioned previously: 4a: Shono,T.; Hayashi, J.; Omoto, H.; Matsumura, Y. Tetrahedron Lett. 1977, 2667-2670. 5a: Ilhyong, R.; Matsumoto, K.; Kameyama, Y.; Ando, M.; Kusumoto, N. J. Am. Chem. Soc. 1993, 115, 12330-12339. 4b: Murphy, R.; Prager, R.; Rolf, H. Aust. J. Chem. 1981, 34, 143-150.
16. 3) δ ppm: 132.6 (CH), 146.0 (CH), 206.2 (C).
17. 3) δ ppm: 129.8 (CH), 158.4 (C), 203.7 (C).