Synthesis of a bifunctional cannabinoid ligand

Abstract

A novel bifunctional classical-nonclassical hybrid cannabinoid has been prepared expeditiously through the Diels–Alder reaction of an ortho-quinomethane.

References

1. J. Busch-Petersen, W. A. Hill, P. Fan, A. Khanolkar, X.-Q. Xie, M. A. Tius and A. Makriyannis, J. Med. Chem., 1996, 39, 3790 and references cited therein.
2. A. Charalambous, G. Yan, D. B. Houston, A. C. Howlett, D. R. Compton, B. R. Martin and A. Makriyannis, J. Med. Chem., 1992, 35, 3076.
3. D. J. Drake, P. Fan, W. A. G. Hill, M. A. Tius and A. Makriyannis, J. Med. Chem., in the press.
4. M. Kobayashi, L. F. Valente and E. Negishi, Synthesis, 1980, 1034.
5. For previous examples of alkyllithium reactions in chlorinated solvent see: K. Maruoka, I. Shimada, H. Imoto and H. Yamamoto, Synlett, 1994, 519.
6. Y. Shen and S. Gao, J. Chem. Soc., Perkin Trans. 1, 1994, 1473.
7. M. T. Reetz, J. Westermann and S.-H. Kyung, Chem. Ber., 1985, 118, 1050.
8. S. J. Dominianni, C. W. Ryan and C. W. DeArmitt, J. Org. Chem., 1977, 42, 344.
9. R. A. Archer, W. B. Blanchard, W. A. Day, D. W. Johnson, E. R. Lavagnino, C. W. Ryan and J. E. Baldwin, J. Org. Chem., 1977, 42, 2277.
10. G. Casiraghi, M. Cornia, G. Casnati, G. Gasparri Fava, M. Ferrari Belicchi and L. Zetta, J. Chem. Soc., Chem. Commun., 1987, 794.
11. Z. G. Lu, N. Sato, S. Inoue and K. Sato, Chem. Lett., 1992, 1237.
12. K. Ishihara, M. Kubota and H. Yamamoto, Synlett, 1996, 1045.
13. M. A. Tius and X.-Q. Gu, J. Chem. Soc., Chem. Commun., 1989, 1171.
14. M. A. Tius, A. M. Makriyannis, X. L. Zou and V. Abadji, Tetrahedron, 1994, 50, 2671.
15. A. J. Papa, J. Org. Chem., 1966, 31, 1426.
16. P. J. Garegg and B. Samuelsson, J. Chem. Soc., Perkin Trans. 1, 1980, 2866.