Triene cyclizations. the total synthesis of pallescensin a.

Synthetic Communications

Volumn 17, Issue 14, 1987, Pages 1655-1665

  Liotta, Dennis ^a   Ott, Walter ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005838218     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397918708063981     Document Type: Article

References (12)

1. G. Cimino, S. DeStefano, A. Guerriero and L. Minale Tetrahedron Lett. 1975, 1475.
2. Hochlowski, J. E.; Walker, R. P.; Ireland, C.; Faulkner, D. J. J. Org. Chem. 1982, 47, 89 and references cited therein.
3. Hochlowski, J. E.; Walker, R. P.; Ireland, C.; Faulkner, D. J. J. Org. Chem. 1982, 47, 89 and references cited therein.
4. Matsumoto, T; Unui, S. Chem. Lett. 1978, 105.
5. Nasipuri, D.; Das, G. J. Chem. Soc., Perkin 1 1979, 2776.
6. Tanis, S. P.; Herrinton, P. M. J. Org. Chem. 1983, 48, 4572.
7. Akita, H.; Oishi, T. Chem. Pharm. Bull. 1981, 29, 1580.
8. Smith, A. B.; Mewshaw, R. J. Org. Chem. 1984, 49, 3685.
9. Ketone 2 was prepared by the reaction of a cis-and trans-mixture of 2, 6-dimethylcyclohexanones with lithium diisopropylamide in THF, followed by methyl iodide. Furan 3 was prepared in a two step process (80% overall yield). See: Liotta, D.; Saindane, M.; Ott, W. Tetrahedron Lett. 1983, 2473.
10. Woodward, R. B.; Hoffmann, R. J. Amer. Chem. Soc. 1965, 87, 395.
11. This process was initially done by performing the pyrolysis in the presence of trace amounts of acetic acid. However, this method proved inconsistent. We thank Professor Andrew Kende (University of Rochester) for suggesting the use of silica gel in place of acetic acid.
12. Liotta, D.; Saindane, M.; Jamison, W. C. L. J.Org.Chem. submitted.