A Novel Sm(II)-Induced Route to Highly Substituted Benzannulated Cyclooctanol Derivatives

Synlett

Volumn 1997, Issue 8, 1997, Pages 995-997

  Khan, Faiz Ahmed ^a   Czerwonka, Regina ^a   Zimmer, Reinhold ^a   Reissig, Hans Ulrich ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002980177     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-934     Document Type: Article

References (32)

1. Selected recent examples: Kaupp, G. Angew. Chem. 1992, 104, 435; Angew. Chem. Int. Ed. Engl. 1992, 31, 422. Wang, Z.; Warder, S. E.; Perrier, H.; Grimm, E. L.; Bernstein, M. A. J. Org. Chem. 1993, 58, 2931. Grimm, E. L.; Lavac, S.; Coutu, M. L. Tetrahedron Lett. 1994, 35, 5369. Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Hanna, I.; Prangé, T.; Zeghuodi, R. Tetrahedron Lett. 1996, 37, 7013. Ihara, M.; Suzuki, S.; Tokunaga, Y.; Takeshita, H.; Fukumoto, K. Chem. Commun. 1996, 1801. Kito, M.; Sakai, T.; Shirahama, H.; Miyashita, M.; Matsuda, F. Synlett 1997, 219. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478.
2. Selected recent examples: Kaupp, G. Angew. Chem. 1992, 104, 435; Angew. Chem. Int. Ed. Engl. 1992, 31, 422. Wang, Z.; Warder, S. E.; Perrier, H.; Grimm, E. L.; Bernstein, M. A. J. Org. Chem. 1993, 58, 2931. Grimm, E. L.; Lavac, S.; Coutu, M. L. Tetrahedron Lett. 1994, 35, 5369. Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Hanna, I.; Prangé, T.; Zeghuodi, R. Tetrahedron Lett. 1996, 37, 7013. Ihara, M.; Suzuki, S.; Tokunaga, Y.; Takeshita, H.; Fukumoto, K. Chem. Commun. 1996, 1801. Kito, M.; Sakai, T.; Shirahama, H.; Miyashita, M.; Matsuda, F. Synlett 1997, 219. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478.
3. Selected recent examples: Kaupp, G. Angew. Chem. 1992, 104, 435; Angew. Chem. Int. Ed. Engl. 1992, 31, 422. Wang, Z.; Warder, S. E.; Perrier, H.; Grimm, E. L.; Bernstein, M. A. J. Org. Chem. 1993, 58, 2931. Grimm, E. L.; Lavac, S.; Coutu, M. L. Tetrahedron Lett. 1994, 35, 5369. Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Hanna, I.; Prangé, T.; Zeghuodi, R. Tetrahedron Lett. 1996, 37, 7013. Ihara, M.; Suzuki, S.; Tokunaga, Y.; Takeshita, H.; Fukumoto, K. Chem. Commun. 1996, 1801. Kito, M.; Sakai, T.; Shirahama, H.; Miyashita, M.; Matsuda, F. Synlett 1997, 219. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478.
4. Selected recent examples: Kaupp, G. Angew. Chem. 1992, 104, 435; Angew. Chem. Int. Ed. Engl. 1992, 31, 422. Wang, Z.; Warder, S. E.; Perrier, H.; Grimm, E. L.; Bernstein, M. A. J. Org. Chem. 1993, 58, 2931. Grimm, E. L.; Lavac, S.; Coutu, M. L. Tetrahedron Lett. 1994, 35, 5369. Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Hanna, I.; Prangé, T.; Zeghuodi, R. Tetrahedron Lett. 1996, 37, 7013. Ihara, M.; Suzuki, S.; Tokunaga, Y.; Takeshita, H.; Fukumoto, K. Chem. Commun. 1996, 1801. Kito, M.; Sakai, T.; Shirahama, H.; Miyashita, M.; Matsuda, F. Synlett 1997, 219. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478.
5. Selected recent examples: Kaupp, G. Angew. Chem. 1992, 104, 435; Angew. Chem. Int. Ed. Engl. 1992, 31, 422. Wang, Z.; Warder, S. E.; Perrier, H.; Grimm, E. L.; Bernstein, M. A. J. Org. Chem. 1993, 58, 2931. Grimm, E. L.; Lavac, S.; Coutu, M. L. Tetrahedron Lett. 1994, 35, 5369. Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Hanna, I.; Prangé, T.; Zeghuodi, R. Tetrahedron Lett. 1996, 37, 7013. Ihara, M.; Suzuki, S.; Tokunaga, Y.; Takeshita, H.; Fukumoto, K. Chem. Commun. 1996, 1801. Kito, M.; Sakai, T.; Shirahama, H.; Miyashita, M.; Matsuda, F. Synlett 1997, 219. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478.
6. Selected recent examples: Kaupp, G. Angew. Chem. 1992, 104, 435; Angew. Chem. Int. Ed. Engl. 1992, 31, 422. Wang, Z.; Warder, S. E.; Perrier, H.; Grimm, E. L.; Bernstein, M. A. J. Org. Chem. 1993, 58, 2931. Grimm, E. L.; Lavac, S.; Coutu, M. L. Tetrahedron Lett. 1994, 35, 5369. Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Hanna, I.; Prangé, T.; Zeghuodi, R. Tetrahedron Lett. 1996, 37, 7013. Ihara, M.; Suzuki, S.; Tokunaga, Y.; Takeshita, H.; Fukumoto, K. Chem. Commun. 1996, 1801. Kito, M.; Sakai, T.; Shirahama, H.; Miyashita, M.; Matsuda, F. Synlett 1997, 219. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478.
7. Selected recent examples: Kaupp, G. Angew. Chem. 1992, 104, 435; Angew. Chem. Int. Ed. Engl. 1992, 31, 422. Wang, Z.; Warder, S. E.; Perrier, H.; Grimm, E. L.; Bernstein, M. A. J. Org. Chem. 1993, 58, 2931. Grimm, E. L.; Lavac, S.; Coutu, M. L. Tetrahedron Lett. 1994, 35, 5369. Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Hanna, I.; Prangé, T.; Zeghuodi, R. Tetrahedron Lett. 1996, 37, 7013. Ihara, M.; Suzuki, S.; Tokunaga, Y.; Takeshita, H.; Fukumoto, K. Chem. Commun. 1996, 1801. Kito, M.; Sakai, T.; Shirahama, H.; Miyashita, M.; Matsuda, F. Synlett 1997, 219. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478.
8. Selected recent examples: Kaupp, G. Angew. Chem. 1992, 104, 435; Angew. Chem. Int. Ed. Engl. 1992, 31, 422. Wang, Z.; Warder, S. E.; Perrier, H.; Grimm, E. L.; Bernstein, M. A. J. Org. Chem. 1993, 58, 2931. Grimm, E. L.; Lavac, S.; Coutu, M. L. Tetrahedron Lett. 1994, 35, 5369. Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Hanna, I.; Prangé, T.; Zeghuodi, R. Tetrahedron Lett. 1996, 37, 7013. Ihara, M.; Suzuki, S.; Tokunaga, Y.; Takeshita, H.; Fukumoto, K. Chem. Commun. 1996, 1801. Kito, M.; Sakai, T.; Shirahama, H.; Miyashita, M.; Matsuda, F. Synlett 1997, 219. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478.
9. Selected recent examples: Kaupp, G. Angew. Chem. 1992, 104, 435; Angew. Chem. Int. Ed. Engl. 1992, 31, 422. Wang, Z.; Warder, S. E.; Perrier, H.; Grimm, E. L.; Bernstein, M. A. J. Org. Chem. 1993, 58, 2931. Grimm, E. L.; Lavac, S.; Coutu, M. L. Tetrahedron Lett. 1994, 35, 5369. Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Hanna, I.; Prangé, T.; Zeghuodi, R. Tetrahedron Lett. 1996, 37, 7013. Ihara, M.; Suzuki, S.; Tokunaga, Y.; Takeshita, H.; Fukumoto, K. Chem. Commun. 1996, 1801. Kito, M.; Sakai, T.; Shirahama, H.; Miyashita, M.; Matsuda, F. Synlett 1997, 219. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478.
10. Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem. 1994, 106, 18; Angew. Chem. Int. Ed. Engl. 1994, 33, 15.
11. Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem. 1994, 106, 18; Angew. Chem. Int. Ed. Engl. 1994, 33, 15.
12. a) Reviews: Kagan, H. B. New J. Chem. 1990, 14, 453. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. Skrydstrop, T. Angew. Chem. 1997, 109, 355; Angew. Chem. Int. Ed. Engl. 1997, 36, 344. Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. b) Synthesis of 8-membered rings promoted by Sm(II): Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705.
13. a) Reviews: Kagan, H. B. New J. Chem. 1990, 14, 453. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. Skrydstrop, T. Angew. Chem. 1997, 109, 355; Angew. Chem. Int. Ed. Engl. 1997, 36, 344. Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. b) Synthesis of 8-membered rings promoted by Sm(II): Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705.
14. a) Reviews: Kagan, H. B. New J. Chem. 1990, 14, 453. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. Skrydstrop, T. Angew. Chem. 1997, 109, 355; Angew. Chem. Int. Ed. Engl. 1997, 36, 344. Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. b) Synthesis of 8-membered rings promoted by Sm(II): Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705.
15. a) Reviews: Kagan, H. B. New J. Chem. 1990, 14, 453. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. Skrydstrop, T. Angew. Chem. 1997, 109, 355; Angew. Chem. Int. Ed. Engl. 1997, 36, 344. Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. b) Synthesis of 8-membered rings promoted by Sm(II): Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705.
16. a) Reviews: Kagan, H. B. New J. Chem. 1990, 14, 453. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. Skrydstrop, T. Angew. Chem. 1997, 109, 355; Angew. Chem. Int. Ed. Engl. 1997, 36, 344. Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. b) Synthesis of 8-membered rings promoted by Sm(II): Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705.
17. a) Reviews: Kagan, H. B. New J. Chem. 1990, 14, 453. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. Skrydstrop, T. Angew. Chem. 1997, 109, 355; Angew. Chem. Int. Ed. Engl. 1997, 36, 344. Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. b) Synthesis of 8-membered rings promoted by Sm(II): Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705.
18. a) Reviews: Kagan, H. B. New J. Chem. 1990, 14, 453. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. Skrydstrop, T. Angew. Chem. 1997, 109, 355; Angew. Chem. Int. Ed. Engl. 1997, 36, 344. Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101. b) Synthesis of 8-membered rings promoted by Sm(II): Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705.
19. Review: Reissig , H.-U. Top Curr. Chem. 1988, 144, 73.
20. Review: Stille, J. K. Angew. Chem. 1986, 98, 504; Angew. Chem. Int. Ed. Engl. 1986, 25, 508.
21. Review: Stille, J. K. Angew. Chem. 1986, 98, 504; Angew. Chem. Int. Ed. Engl. 1986, 25, 508.
22. Khan, F. A.; Czerwonka, R.; Reissig, H.-U. Synlett 1996, 533.
23. For a general procedure for ring cleavage of related systems, see: Kunkel, E.; Reichelt, I.; Reissigm H.-U. Liebigs Ann. Chem. 1984, 802.
24. For a typical alkylation procedure, see: Reichelt, I.; Reissig, H.-U. Liebigs Ann. Chem. 1984, 531.
25. This compound is easily available in four steps starting from phthalide.
26. These conditions are similar to those employed by Molander and McKie for the synthesis of less functionalized cyclooctanols (see ref. 3b).
27. The diastereomers have been used either as 1:1 mixture or as separated pure compounds.
28. The NMR data of 1b are so far not conclusive since the other diastereomers are not available for comparison.
29. 2 (230.3): calcd. C 78.23, H 7.88; found C 78.62, H 8.27.
30. The structure of 7c was unequivocally confirmed by an x-ray analysis: Khan, F. A.; Zimmer, R.; Reissig, H.-U. Zahn, G. Z. Kristallogr. 1997, submitted.
31. There are at least two mechanistic pathways leading to 9 which will be discussed in a full paper. Compound 10 is probably the result of a Lewis acid promoted rearrangement of 2c. 16) For related observations in ketyl-olefin cyclizations leading to cyclopentane derivatives see: Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265.
32. For α-hydroxylation of enolates with oxygen see: Jones, A. B. in Comprehensive Organic Syntheses (Eds. Trost, B. M.; Fleming, I.) Vol. 7, p. 151, Pergamon Press, Oxford 1991.