Synthesis of highly functionalized polycyclics via Pd-catalyzed intramolecular coupling of aryl/vinylic halides, non-conjugated dienes and nucleophiles

Synlett

Volumn , Issue 7, 1998, Pages 748-750

  Han, Xiaojun ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002917117     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1772     Document Type: Article

References (21)

1. Larock, R. C.; Lu, Y. D.; Bain, A. C. J. Org. Chem. 1991, 56, 4589.
2. Larock, R. C.; Wang, Y., Lu, Y. D.; Russell, C. E. J. Org. Chem. 1995, 59, 8107.
3. Iodide 1 was prepared by the Mitsunobu reaction (Nakano, J.; Mimura, M.; Hayashida, M.; Kimura, K.; Nakanishi, T. Heterocycles 1983, 20, 1975) of 2-iodophenol with 2,5-cyclohexadienyl methanol.
4. 3.
5. Iodides 9, 13, 15 and 19 were prepared by the reaction of methyl 2,5-cyclohexadienyl carboxylate enolate (Cho, J. H.; Djerassi, C. J. Org. Chem. 1987, 52, 4517) with the corresponding allylic bromides, made from the reaction of the corresponding allylic alcohol
6. 3. Iodide 11 was obtained by the DIBAL-H reduction of iodide 9.
7. 8. (Chemical Equation Presented)
8. 4, and decanted. The solvent was evaporated in vacuo and the product was isolated by flash chromatography (EtOAc/hexanes) on a silica gel column.
9. Connell, R. D.; Rein, T.; Akermark, B.; Helquist, P. J. Org. Chem. 1988, 53, 3845 and references therein.
10. Trost, B. M.; Organ, M. G.; O'Doherty, G. A. J. Am. Chem. Soc. 1995, 117, 9662.
11. Larock, R. C.; Wang, Y.; Lu, Y., publication in preparation.
12. Larock, R. C.; Mitchell, M. A. J. Am. Chem. Soc. 1976, 98, 6718.
13. Larock, R. C.; Mitchell, M. A. J. Am. Chem. Soc. 1978, 100, 180.
14. Larock, R. C.; Takagi, K.; Hershberger, S. S.; Mitchell, M. A. Tetrahedron Lett. 1981, 22, 5231.
15. Larock, R. C.; Song, S. Bull. Korean Chem. Soc. 1996, 17, 877.
16. Larock, R. C.; Yum, E. K. Synlett 1990, 529.
17. Larock, R. C.; Song, H.; Kim, S.; Jacobson, R. A. J. Chem. Soc., Chem. Commun. 1987, 834.
18. Larock, R. C.; Varaprath, S. J. Org. Chem. 1984, 49, 3432.
19. Shibasaki, M. In Advances in Metal-Organic Chemistry, Liebeskind, L. S., Ed; JAI Press: Greenwich, 1996; Vol. 5, p119-151.
20. Kondo, K.; Sodeoka, M.; Mori, M.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 4219.
21. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738.