A Reiterative Synthesis of Trans-Fused Polypyrans via Tungsten Pentacarbonyl-Promoted Alkynol Endocyclization

Journal of Organic Chemistry

Volumn 63, Issue 11, 1998, Pages 3680-3682

  Bowman, Jason L ^a   McDonald, Frank E ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001689433     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980058k     Document Type: Article

References (23)

1. (a) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897.
2. (b) Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953.
3. Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 588.
4. Krishna Prasad, A. V.; Shimizu, Y. J. Am. Chem. Soc. 1989, 111, 6476.
5. For other reiterative approaches to forming trans-fused polypyrans, see (a) Kozikowski, A. P.; Ghosh, A. K. J. Org. Chem. 1985, 50, 3017. (b) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158.
6. For other reiterative approaches to forming trans-fused polypyrans, see (a) Kozikowski, A. P.; Ghosh, A. K. J. Org. Chem. 1985, 50, 3017. (b) Mori, Y.; Yaegashi, K.; Furukawa, H. J. Am. Chem. Soc. 1996, 118, 8158.
7. McDonald, F. E.; Bowman, J. L. Tetrahedron Lett. 1996, 37, 4675.
8. (a) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363.
9. (b) McDonald, F. E.; Schultz, C. C.; Chatterjee, A. K. Organometallics 1995, 14, 3628.
10. For a successful example of dihydropyran formation via molybdenum-catalyzed cycloisomerization, see McDonald, F. E.; Zhu H. Y. H. Tetrahedron 1997, 53, 11061.
11. Dotz, K. H.; Sturm, W.; Alt, H. G. Organometallics 1987, 6, 1424.
12. Bruce, M. I.; Swincer, A. G.; Thomson, B. J.; Wallis, R. C. Aust. J. Chem. 1980, 33, 2605.
13. For syntheses of six-membered cyclic tungsten oxacarbenes via annulation strategies, see (a) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 9855. (b) Aoki, S.; Fujimura, T.; Nakamura, E. J. Am. Chem. Soc. 1992, 114, 2985.
14. For syntheses of six-membered cyclic tungsten oxacarbenes via annulation strategies, see (a) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 9855. (b) Aoki, S.; Fujimura, T.; Nakamura, E. J. Am. Chem. Soc. 1992, 114, 2985.
15. Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154.
16. Boeckman, R. K., Jr.; Bruza, K. J. Tetrahedron 1981, 37, 3997.
17. Kocienski, P.; Yeates, C. Tetrahedron Lett. 1983, 24, 3905.
18. Svatos, A.; Attygalle, A. B.; Meinwald, J. Tetrahedron Lett. 1994, 35, 9497.
19. Although we could selectively react the enol ether 13 with borane when the alkyne was protected as a hexacarbonyl dicobalt complex, the overall conversion to 16 was disappointingly low (ref 4), However, this stereochemically unambiguous synthesis provided confirmation of the relative stereochemistry of 16 prepared as shown in Scheme 3.
20. (a) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976.
21. (b) Bennek, J. A.; Gray, G. R. J. Org. Chem. 1987, 52, 892.
22. Chromatography on basic alumina proved insufficient for the separation of 17 from inorganic tungsten byproducts.
23. Triethylsilane reduction at this stage with TMSOTf in acetonitrile at -30 °C gave several diastereomers and resulted in a lower overall yield of 21.