Competing Diels-Alder intramolecular pathways from cross-conjugated trienes: Fused hydrindenones (bicyclo[4.3.0]nonenones) vs. bridged-ring (bicyclo[3.3.1]nonenones) adducts from a diene-transmissive precursor

Canadian Journal of Chemistry

Volumn 83, Issue 6-7, 2005, Pages 559-568

  Clay, Matthew D ^a   Riber, Ditte ^a,b   Fallis, Alex G ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

^b AARHUS UNIVERSITY   (Denmark)

Author keywords

Bicyclo 3.3.1 nonenone; Diels Alder; Hydrindane; Intramolecular cycloaddition; Pentadienylation

Indexed keywords

ISOMERS; ORGANIC POLYMERS;

DIELS-ALDER; HYDRINDANE; PENTADIENYLATION;

REACTION KINETICS;

ALKADIENE; ALKENE; BICYCLO COMPOUND; BICYCLO[3.3.1]NONENONE DERIVATIVE; BICYCLO[4.3.0]NONENONE DERIVATIVE; BRIDGED COMPOUND; DECALIN DERIVATIVE; DESOGESTREL; FUSED HETEROCYCLIC RINGS; HYDRINDENONE DERIVATIVE; INDAN DERIVATIVE; ISOASCORBIC ACID; KETONE; STEROID; TETRAENONE; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATION; DIELS ALDER REACTION; ISOMER; PRECURSOR; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 29244456406     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v05-055     Document Type: Article

References (17)

1. (a) E.J. Corey and A.X. Huang. J. Am. Chem. Soc. 121, 710 (1999);
2. (b) Q.-Y. Hu, P.D. Rege, and E.J. Corey. J. Am. Chem. Soc. 126, 5984 (2004).
3. (a) C. Martin, N. Macintosh, N. Lamb, and A.G. Fallis. Org. Lett. 3, 1021 (2001);
4. (b) A. Melekhov, P. Forgione, S. Legoupy, and A.G. Fallis. Org. Lett. 2, 2793 (2000);
5. T. Wong, P.D. Wilson, S. Woo, and A.G. Fallis. Tetrahedron Lett. 38, 7045 (1997).
6. S. Woo, S. Legoupy, S. Parra, and A.G. Fallis. Org. Lett. 1, 1013 (1999).
7. S. Woo, N. Squires, and A.G. Fallis. Org. Lett. 1, 573 (1999).
8. D. Kim and Y.K. Lee. Tetrahedron Lett. 32, 6885 (1991).
9. B.B. Snider and T.C. Kirk. J. Am. Chem. Soc. 105, 2364 (1983).
10. (a) S.A. Bal and P. Helquist. Tetrahedron Lett. 22, 3933 (1981);
11. (b) M.E. Jung and K.M. Halweg. Tetrahedron Lett. 22, 3929 (1981);
12. (c) J. Shiina and S. Nishiyama. Tetrahedron, 59, 6039 (2003).
13. J. Endrikat, M. Cronin, C. Gerlinger, A. Ruebig, W. Schmidt, and B. Dusterberg. Contraception, 64, 201 (2001).
14. A.B. Northrup and D.W.C. MacMillan. J. Am. Chem. Soc. 124, 2458 (2002).
15. N. Cohen, B.L. Banner, A.J. Laurenzano, and L. Carozza. Org. Synth. 63, 127 (1984).
16. S.D. Meyer and S.L. Schreiber. J. Org. Chem. 59, 7549 (1994).
17. A.G. Fallis. Can. J. Chem. 62, 183 (1984).