Total synthesis of the tricyclic sesquiterpene (±)-ceratopicanol. An illustration of the holosynthon concept

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3576-3577

  Baralotto, Christophe ^a   Chanon, Michel ^a   Julliard, Michel ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CERATOPICANOL; SESQUITERPENE; UNCLASSIFIED DRUG;

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

EID: 0029941266     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960382k     Document Type: Article

References (22)

1. Hansen, H. P.; Abraham, W. R. Tetrahedron 1988, 44, 2175.
2. Mehta, G; Karra, S. R. J. Chem. Soc., Chem. Commun. 1991, 1367.
3. Clive, D. L. J.; Magnuson, S. R. Tetrahedron Lett. 1995, 36, 15.
4. Hayano, K.; Ohfune, Y.; Shirahama, H.; Matsumoto, T. Helv. Chim. Acta 1981, 64, 1347.
5. Holosynthon: structural entity specifically designed to make possible a great change in complexity or similarity (between this structural entity and its successor) when a one-pot reaction or a set of reactions are applied to it. (a) Barone, R.; Chanon, M. In Computer Aids to Chemistry; Vernin, G., Chanon, M., Eds.; Horwood: Chichester, 1986; p 69. (b) Barberis, F.; Barone, R.; Arbelot, M.; Baldy, A.; Chanon, M. J. Chem. Inf. Comput. Sci. 1995, 34, 467. (c) Lacourcelle, C.; Poite, J. C.; Baldy, A.; Jaud, J.; Negrel, J. C.; Chanon, M. Acta Chem. Scand. 1993, 47, 92. (d) See also a special issue: Chem. Rev. 1996, 96, 1.
6. Holosynthon: structural entity specifically designed to make possible a great change in complexity or similarity (between this structural entity and its successor) when a one-pot reaction or a set of reactions are applied to it. (a) Barone, R.; Chanon, M. In Computer Aids to Chemistry; Vernin, G., Chanon, M., Eds.; Horwood: Chichester, 1986; p 69. (b) Barberis, F.; Barone, R.; Arbelot, M.; Baldy, A.; Chanon, M. J. Chem. Inf. Comput. Sci. 1995, 34, 467. (c) Lacourcelle, C.; Poite, J. C.; Baldy, A.; Jaud, J.; Negrel, J. C.; Chanon, M. Acta Chem. Scand. 1993, 47, 92. (d) See also a special issue: Chem. Rev. 1996, 96, 1.
7. Holosynthon: structural entity specifically designed to make possible a great change in complexity or similarity (between this structural entity and its successor) when a one-pot reaction or a set of reactions are applied to it. (a) Barone, R.; Chanon, M. In Computer Aids to Chemistry; Vernin, G., Chanon, M., Eds.; Horwood: Chichester, 1986; p 69. (b) Barberis, F.; Barone, R.; Arbelot, M.; Baldy, A.; Chanon, M. J. Chem. Inf. Comput. Sci. 1995, 34, 467. (c) Lacourcelle, C.; Poite, J. C.; Baldy, A.; Jaud, J.; Negrel, J. C.; Chanon, M. Acta Chem. Scand. 1993, 47, 92. (d) See also a special issue: Chem. Rev. 1996, 96, 1.
8. Holosynthon: structural entity specifically designed to make possible a great change in complexity or similarity (between this structural entity and its successor) when a one-pot reaction or a set of reactions are applied to it. (a) Barone, R.; Chanon, M. In Computer Aids to Chemistry; Vernin, G., Chanon, M., Eds.; Horwood: Chichester, 1986; p 69. (b) Barberis, F.; Barone, R.; Arbelot, M.; Baldy, A.; Chanon, M. J. Chem. Inf. Comput. Sci. 1995, 34, 467. (c) Lacourcelle, C.; Poite, J. C.; Baldy, A.; Jaud, J.; Negrel, J. C.; Chanon, M. Acta Chem. Scand. 1993, 47, 92. (d) See also a special issue: Chem. Rev. 1996, 96, 1.
9. De Keukeleire, D.; He, S. L. Chem. Rev. 1993, 93, 359.
10. Hoffmann, N.; Pete, J. P. Tetrahedron Lett. 1995, 36, 2623.
11. (a) Wender, P. A.; Howbert, J. J. J. Am. Chem. Soc. 1981, 103, 688.
12. (b) Wender, P. A.; Dreyer, G. B. Tetrahedron 1981, 37, 4445.
13. (c) Wender, P. A.; Dreyer, G. B. J. Am. Chem. Soc. 1982, 104, 5805.
14. (d) Wender, P. A.;Von Geldern, T. W.; Levine, B. H. J. Am. Chem. Soc. 1988, 110, 4858.
15. (e) Wender, P. A.; Singh, S. K. Tetrahedron Lett. 1990, 31, 2520.
16. Cornelisse, J. Chem. Rev. 1993, 93, 615.
17. The angular isomer 5b could be recycled by irradiation to produce a mixture of angular and linear isomers.
18. Hall, S. S.; Mc Enroe, F. J. J. Org. Chem. 1975, 40, 271.
19. Wender, P. A.; Howbert, J. J. Tetrahedron Lett. 1975, 23, 3983.
20. Salmond, W. A.; Barta, M. A.; Havens, J. L. J. Org. Chem. 1978, 43, 2057.
21. Shibasaki, M.; Mase, T.; Ikegami, S. J. Am. Chem. Soc. 1986, 108, 2090.
22. For a theoretical treatment of the photocycloaddition process see: Houk, K. N. Pure Appl. Chem. 1982, 54, 1633-1650.