Regioselective Addition of Grignard Reagents to Substituted Tropones

Synthetic Communications

Volumn 25, Issue 24, 1995, Pages 4115-4122

  Rigby, James H ^a   de Sainte Claire, Valérie ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TROPONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029610905     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397919508011490     Document Type: Article

References (12)

1. Rigby, J. H. in “Studies in Natural Products Chemistry” Rahman, A., Ed., Elsevier: Amsterdam, Volume 1 (Part A), 1988, pp. 545–576.
2. Rigby, J. H. Acc. Chem. Res. 1993, 26, 579.
3. Feldman, K. S.; Wu, M. -J.; Rotella, D. P. J. Am. Chem. Soc. 1989, 111, 6457.
4. Chapman, O. L.; Pasto, D. J.; Griswold, A. A. Tetrahedron Lett. 1962, 84, 121
5. Nozoe, T.; Mukai, T.; Minegishi, J. Proc. Japan Acad. 1951, 27, 419.
6. A detailed regiochemical study of the [6π + 4π] cycloaddition of substituted tropones has appeared: Garst, M. E.; Roberts, V. A.; Houk, K. N.; Rondon, N. G. J. Am. Chem. Soc. 1984, 106, 3882.
7. Roberts, V. A.; Garst, M. E.; Torres, N. E. J. Org. Chem. 1984, 49, 1136.
8. Chapman, O. L.; Meinwald, J. J. Am. Chem. Soc. 1958, 80, 633.
9. The methodology of Garst and Roberts was used to prepare both 3- and 4-ethoxycarbonyl tropone. Garst, M. E.; Roberts, V. A. J. Org. Chem. 1982, 47, 2188.
10. For methods to prepare highly substituted tropones and tropolones, consult: a) Davies, H. W. L.; Clark, T. J. Tetrahedron 1994, 50, 9883.
11. Banwell, M. G. Aust. J. Chem. 1991, 44, 1.
12. For general experimental details, please consult: Rigby, J. H.; Qabar, M.; Ahmed, G.; Hughes, R. C. Tetrahedron 1993, 49, 10219.