Ethyl (1R*,3aS*,7aS*)-octahydro-7a-methyl-7-oxo1h-indene-1-acetate using tandem reactions

Synthetic Communications

Volumn 26, Issue 10, 1996, Pages 1969-1975

  Bunce, Richard A ^a   Harris, Christina R ^a  

^a OKLAHOMA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDENE DERIVATIVE; OCTAHYDRO 7A METHYL 7 OXO 1H INDENE 1 ACETIC ACID ETHYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029905428     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003551     Document Type: Article

References (14)

1. Taken from the senior research thesis of C.R.H., 1992.
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7. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736.
8. Friebolin, H. "Basic One- and Two-Dimensional NMR Spectroscopy," VCH: New York, 1991, pp. 251-261.
9. Other 5-6 and 6-6 fused ring systems are available using this methodology, but selectivities in the final ring closure ranged from only 1:1 to 3:1 and separation of isomers was difficult; the 5-5 system did not close to any appreciable extent presumably due to ring strain and the reversibility of the Michael reaction.
10. Leopold, E. J. J. Org. Chem. 1982, 47, 4592-4593.
11. Degenhardt, C. R. J. Org. Chem. 1980, 45, 2763-2766.
12. (a) Maercker, A. Organic React. 1965, 14, 270-490.
13. (b) Fieser, L. F.; Fieser, M. "Reagents for Organic Synthesis," Wiley: New York, 1967; Vol. 1, pp. 112-114.
14. Bunce, R. A.; Dowdy, E. D.; Jones, P. B.; Holt, E. M. J. Org. Chem. 1993, 55, 7143-7148.