A New General Method for the Construction of Angular Triquinanes from 4-Allylcyclobutenones. Rearrangement of Linear Triquinanes to the Angular Isomers

Journal of Organic Chemistry

Volumn 62, Issue 14, 1997, Pages 4554-4555

  MacDougall, James M ^a   Moore, Harold W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANONE DERIVATIVE; QUINIC ACID; SQUARIC ACID DERIVATIVE; TRIQUINANE DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL STRUCTURE; DIASTEREOISOMER; NOTE; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0030814737     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970609r     Document Type: Article

References (26)

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12. For reviews on polyquinane chemistry, see: (a) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry. Reactivity and Structure Concepts in Organic Chemistry; Springer-Verlag: New York, 1987; Vol. 26. (b) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (c) Paquette, L. A. Top. Curr. Chem. 1979, 79, 43. (d) Hudlicky, T.; Rulin, F.; Lovelace, T. C.; Reed, J. W. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 3, pp 3-72.
13. For reviews on polyquinane chemistry, see: (a) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry. Reactivity and Structure Concepts in Organic Chemistry; Springer-Verlag: New York, 1987; Vol. 26. (b) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (c) Paquette, L. A. Top. Curr. Chem. 1979, 79, 43. (d) Hudlicky, T.; Rulin, F.; Lovelace, T. C.; Reed, J. W. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 3, pp 3-72.
14. For reviews on polyquinane chemistry, see: (a) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry. Reactivity and Structure Concepts in Organic Chemistry; Springer-Verlag: New York, 1987; Vol. 26. (b) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (c) Paquette, L. A. Top. Curr. Chem. 1979, 79, 43. (d) Hudlicky, T.; Rulin, F.; Lovelace, T. C.; Reed, J. W. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 3, pp 3-72.
15. For reviews on polyquinane chemistry, see: (a) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry. Reactivity and Structure Concepts in Organic Chemistry; Springer-Verlag: New York, 1987; Vol. 26. (b) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. (c) Paquette, L. A. Top. Curr. Chem. 1979, 79, 43. (d) Hudlicky, T.; Rulin, F.; Lovelace, T. C.; Reed, J. W. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 3, pp 3-72.
16. For the synthesis of angular triquinanes, see: (a) Tormo, J.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Tetrahedron 1996, 52, 14021.
17. (b) Yadav, J. Spraveen Kumar, T. K.; Gadgil, V. R. Tetrahedron Lett. 1992, 33, 3687. (c) Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett. 1992, 33, 3879. (d) Hollingworth, G. J., Pattenden, G.; Schulz, D. J. Aust. Chem. 1995, 48, 381. (e) Ihara, M.; Tokunaga, Y.; Taniguchi, N.; Fukumato, K. J. Org. Chem. 1991, 56, 5281. (f) Kumar, M. S.; Rao, J. M. Indian J. of Chem. 1994, 33B, 729.
18. (b) Yadav, J. SPraveen Kumar, T. K.; Gadgil, V. R. Tetrahedron Lett. 1992, 33, 3687. (c) Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett. 1992, 33, 3879. (d) Hollingworth, G. J., Pattenden, G.; Schulz, D. J. Aust. Chem. 1995, 48, 381. (e) Ihara, M.; Tokunaga, Y.; Taniguchi, N.; Fukumato, K. J. Org. Chem. 1991, 56, 5281. (f) Kumar, M. S.; Rao, J. M. Indian J. of Chem. 1994, 33B, 729.
19. (b) Yadav, J. SPraveen Kumar, T. K.; Gadgil, V. R. Tetrahedron Lett. 1992, 33, 3687. (c) Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett. 1992, 33, 3879. (d) Hollingworth, G. J., Pattenden, G.; Schulz, D. J. Aust. Chem. 1995, 48, 381. (e) Ihara, M.; Tokunaga, Y.; Taniguchi, N.; Fukumato, K. J. Org. Chem. 1991, 56, 5281. (f) Kumar, M. S.; Rao, J. M. Indian J. of Chem. 1994, 33B, 729.
20. (b) Yadav, J. SPraveen Kumar, T. K.; Gadgil, V. R. Tetrahedron Lett. 1992, 33, 3687. (c) Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett. 1992, 33, 3879. (d) Hollingworth, G. J., Pattenden, G.; Schulz, D. J. Aust. Chem. 1995, 48, 381. (e) Ihara, M.; Tokunaga, Y.; Taniguchi, N.; Fukumato, K. J. Org. Chem. 1991, 56, 5281. (f) Kumar, M. S.; Rao, J. M. Indian J. of Chem. 1994, 33B, 729.
21. (b) Yadav, J. SPraveen Kumar, T. K.; Gadgil, V. R. Tetrahedron Lett. 1992, 33, 3687. (c) Franck-Neumann, M.; Miesch, M.; Gross, L. Tetrahedron Lett. 1992, 33, 3879. (d) Hollingworth, G. J., Pattenden, G.; Schulz, D. J. Aust. Chem. 1995, 48, 381. (e) Ihara, M.; Tokunaga, Y.; Taniguchi, N.; Fukumato, K. J. Org. Chem. 1991, 56, 5281. (f) Kumar, M. S.; Rao, J. M. Indian J. of Chem. 1994, 33B, 729.
22. For methods that have been applied to the synthesis of both linear and angular triquinanes, see: (a) Enholm, E. J.; Jia, Z. J. J. Org. Chem. 1997, 62, 174. (b) Meyer, C.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1996, 37, 857. (c) Maki, S.; Toyoda, K.; Mori, T.; Kosemura, S.; Yamamura, S. Tetrahedron Lett. 1994, 35, 4817. (d) Cosstick, K.; Gilbert, A. J. Chem. Soc., Perkin Trans. 1 1989, 1541.
23. For methods that have been applied to the synthesis of both linear and angular triquinanes, see: (a) Enholm, E. J.; Jia, Z. J. J. Org. Chem. 1997, 62, 174. (b) Meyer, C.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1996, 37, 857. (c) Maki, S.; Toyoda, K.; Mori, T.; Kosemura, S.; Yamamura, S. Tetrahedron Lett. 1994, 35, 4817. (d) Cosstick, K.; Gilbert, A. J. Chem. Soc., Perkin Trans. 1 1989, 1541.
24. For methods that have been applied to the synthesis of both linear and angular triquinanes, see: (a) Enholm, E. J.; Jia, Z. J. J. Org. Chem. 1997, 62, 174. (b) Meyer, C.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1996, 37, 857. (c) Maki, S.; Toyoda, K.; Mori, T.; Kosemura, S.; Yamamura, S. Tetrahedron Lett. 1994, 35, 4817. (d) Cosstick, K.; Gilbert, A. J. Chem. Soc., Perkin Trans. 1 1989, 1541.
25. For methods that have been applied to the synthesis of both linear and angular triquinanes, see: (a) Enholm, E. J.; Jia, Z. J. J. Org. Chem. 1997, 62, 174. (b) Meyer, C.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1996, 37, 857. (c) Maki, S.; Toyoda, K.; Mori, T.; Kosemura, S.; Yamamura, S. Tetrahedron Lett. 1994, 35, 4817. (d) Cosstick, K.; Gilbert, A. J. Chem. Soc., Perkin Trans. 1 1989, 1541.
26. An arene-olefin metaphotocycloaddition gave a mixture of cyclopropane-fused linear and angular triquinanes that were photo-chemically interconvertible: Wender, P. A.; Singh, S. K. Tetrahedron Lett. 1985, 5987.