Synthesis of novel tetracycles via an intramolecular Heck reaction with anti-hydride elimination

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3679-3682

  Lautens, Mark ^a   Fang, Yuan Qing ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

NAPHTHALENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; HECK REACTION; REACTION ANALYSIS;

EID: 0142042916     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035354k     Document Type: Article

References (30)

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2. ARO using heteroatom nucleophiles: (b) Lautens, M.; Fagnou, K.; Yang, D. J. Am. Chem. Soc. 2003, 125, in press. (c) Lautens, M.; Fagnou, K.; Taylor, M.; Rovis, T. J. Organomet. Chem. 2001, 624, 259-270.
3. ARO using heteroatom nucleophiles: (b) Lautens, M.; Fagnou, K.; Yang, D. J. Am. Chem. Soc. 2003, 125, in press. (c) Lautens, M.; Fagnou, K.; Taylor, M.; Rovis, T. J. Organomet. Chem. 2001, 624, 259-270.
4. ARO using carbon-based nucleophiles: (d) Lautens, M.; Dockendorff, C.; Fagnou, K.; Malicki, A. Org. Lett. 2002, 4, 1311-1314. (e) Lautens, M.; Renaud, J.-L.; Hiebert, S. J. Am. Chem. Soc. 2000, 122, 1804-1805.
5. ARO using carbon-based nucleophiles: (d) Lautens, M.; Dockendorff, C.; Fagnou, K.; Malicki, A. Org. Lett. 2002, 4, 1311-1314. (e) Lautens, M.; Renaud, J.-L.; Hiebert, S. J. Am. Chem. Soc. 2000, 122, 1804-1805.
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8. Lautens, M.; Fagnou, K.; Taylor, M. Org. Lett. 2000, 2, 1677-1679.
9. For reviews, see: (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066. (b) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411. (c) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371-7395.
10. For reviews, see: (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066. (b) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411. (c) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371-7395.
11. For reviews, see: (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066. (b) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411. (c) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371-7395.
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13. Some recent examples: (a) Maeda, K.; Farrington, E. J.; Galardon, E.; John, B. D.; Brown, J. M. Adv. Synth. Catal. 2002, 344, 104-109. (b) Shea, K. M.; Lee, K. L.; Danheiser, R. L. Org. Lett. 2000, 2, 2353-2356. (c) For examples before 1999, see: Ikeda, M.; El Bialy, S. A. A.; Yakura, T. Heterocycles 1999, 51, 1957-1970 and references therein.
14. Some recent examples: (a) Maeda, K.; Farrington, E. J.; Galardon, E.; John, B. D.; Brown, J. M. Adv. Synth. Catal. 2002, 344, 104-109. (b) Shea, K. M.; Lee, K. L.; Danheiser, R. L. Org. Lett. 2000, 2, 2353-2356. (c) For examples before 1999, see: Ikeda, M.; El Bialy, S. A. A.; Yakura, T. Heterocycles 1999, 51, 1957-1970 and references therein.
15. Some recent examples: (a) Maeda, K.; Farrington, E. J.; Galardon, E.; John, B. D.; Brown, J. M. Adv. Synth. Catal. 2002, 344, 104-109. (b) Shea, K. M.; Lee, K. L.; Danheiser, R. L. Org. Lett. 2000, 2, 2353-2356. (c) For examples before 1999, see: Ikeda, M.; El Bialy, S. A. A.; Yakura, T. Heterocycles 1999, 51, 1957-1970 and references therein.
16. Review: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
17. (a) Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10-11.
18. (b) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989-7000.
19. (c) Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677-2678.
20. Unprotected substrates yielded a complicated mixture of products. Other protecting groups such as Me, MOM, and TMS gave incomplete conversion or low yields of the desired Heck product even under optimized conditions.
21. 3: Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295-4298.
22. (a) Adams, N. J.; Bargon, J.; Brown, J. M.; Farrington, E. J.; Galardon, E.; Giernoth, R.; Heinrich, H.; John, B. D.; Maeda, K. Pure Appl. Chem. 2001, 73, 343-346.
23. (b) ref 3a.
24. (c) Although the mechanism via epimerization of the benzylic center by an external Pd(0) attack followed by cis-elimination cannot be completely excluded, we believe that this mechanism is unlikely because of steric hindrance. Lau, K. S. Y.; Wong, P. K.; Stille, J. K. J. Am. Chem. Soc. 1976, 98, 5832-5840.
25. (a) Gurtler, C.; Buchwald, S. L. Chem. Eur. J. 1999, 5, 3107-3112.
26. (b) ref 8b.
27. 2 was used. When this catalyst was used, the TON was lower than 10 and a palladium mirror was formed inside the reaction flask.
28. Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7.
29. All substrates are racemates obtained from the Rh-catalyzed ring-opening reaction followed by TBS protection. See Supporting Information for their preparation.
30. 3 complexes: Dongol, K. G. ; Matsubara, K.; Mataka, S.; Thiemann, T. Chem. Commun. 2002, 3060-3061.