Stereocontrolled synthesis of trisubstituted tetrahydropyrans [3]

Journal of the American Chemical Society

Volumn 121, Issue 5, 1999, Pages 1092-1093

  Cloninger, Mary J ^a   Overman, Larry E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROPYRAN DERIVATIVE;

CHEMICAL REACTION; CHEMICAL STRUCTURE; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0033540691     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9838007     Document Type: Letter

References (34)

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5. For reviews of the Prins reaction, see: (a) Adams, D. R.; Bhaynagar, S. D. Synthesis 1977, 661. (b) Snider, B. B. The Prins and Carbonyl Ene Reactions. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, pp 527-561.
6. For representative recent examples, see: (a) Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022. (b) Markó, I. E.; Dobbs, A. P.; Scheirmann, V.; Chellé, F.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899. (c) Hu, Y.; Skalitzky, D. J.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 8679. (d) Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141. (e) Masuyama, Y.; Gotoh, S.-y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989. (f) Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115. (g) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911.
7. For representative recent examples, see: (a) Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022. (b) Markó, I. E.; Dobbs, A. P.; Scheirmann, V.; Chellé, F.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899. (c) Hu, Y.; Skalitzky, D. J.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 8679. (d) Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141. (e) Masuyama, Y.; Gotoh, S.-y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989. (f) Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115. (g) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911.
8. For representative recent examples, see: (a) Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022. (b) Markó, I. E.; Dobbs, A. P.; Scheirmann, V.; Chellé, F.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899. (c) Hu, Y.; Skalitzky, D. J.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 8679. (d) Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141. (e) Masuyama, Y.; Gotoh, S.-y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989. (f) Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115. (g) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911.
9. For representative recent examples, see: (a) Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022. (b) Markó, I. E.; Dobbs, A. P.; Scheirmann, V.; Chellé, F.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899. (c) Hu, Y.; Skalitzky, D. J.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 8679. (d) Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141. (e) Masuyama, Y.; Gotoh, S.-y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989. (f) Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115. (g) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911.
10. For representative recent examples, see: (a) Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022. (b) Markó, I. E.; Dobbs, A. P.; Scheirmann, V.; Chellé, F.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899. (c) Hu, Y.; Skalitzky, D. J.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 8679. (d) Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141. (e) Masuyama, Y.; Gotoh, S.-y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989. (f) Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115. (g) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911.
11. For representative recent examples, see: (a) Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022. (b) Markó, I. E.; Dobbs, A. P.; Scheirmann, V.; Chellé, F.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899. (c) Hu, Y.; Skalitzky, D. J.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 8679. (d) Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141. (e) Masuyama, Y.; Gotoh, S.-y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989. (f) Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115. (g) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911.
12. For representative recent examples, see: (a) Rychnovsky, S. D.; Yang, G.; Hu, Y.; Khire, U. R. J. Org. Chem. 1997, 62, 3022. (b) Markó, I. E.; Dobbs, A. P.; Scheirmann, V.; Chellé, F.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899. (c) Hu, Y.; Skalitzky, D. J.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 8679. (d) Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1996, 37, 141. (e) Masuyama, Y.; Gotoh, S.-y.; Kurusu, Y. Synth. Commun. 1995, 25, 1989. (f) Lolkema, L.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115. (g) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911.
13. For brief reviews of our early work in this area, see: (a) Overman, L. E. Lect. Heterocycl. Chem. 1985, 8, 59. (b) Overman, L. E. Acc. Chem. Res. 1992, 25, 352.
14. For brief reviews of our early work in this area, see: (a) Overman, L. E. Lect. Heterocycl. Chem. 1985, 8, 59. (b) Overman, L. E. Acc. Chem. Res. 1992, 25, 352.
15. For representative recent examples, see: (a) Ando, S.; Minor, K. P.; Overman, L. E. J. Org. Chem. 1997, 62, 6379. (b) Minor, K. P.; Overman, L. E. Tetrahedron 1997, 53, 8927. (c) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391.
16. For representative recent examples, see: (a) Ando, S.; Minor, K. P.; Overman, L. E. J. Org. Chem. 1997, 62, 6379. (b) Minor, K. P.; Overman, L. E. Tetrahedron 1997, 53, 8927. (c) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391.
17. For representative recent examples, see: (a) Ando, S.; Minor, K. P.; Overman, L. E. J. Org. Chem. 1997, 62, 6379. (b) Minor, K. P.; Overman, L. E. Tetrahedron 1997, 53, 8927. (c) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391.
18. 2 at -25°C under the original reaction conditions, establishing that this compound is not an intermediate on the pathway to 7.
19. Brown, H. C.; Kanner, B. J. Am. Chem. Soc. 1966, 88, 986.
20. 1H NMR spectrum showed only 5 and 6.
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23. 4) and concentrated, and the resulting oil was purified on silica gel to give acetyltetrahydropyran 7.
24. Although the transformation could be carried out with 0.25 equiv of TfOH (Table 1, preparation of 7c,d,g), reactions using 0.5 equiv TfOH were generally higher yielding (Table 1, preparation of 7a,b,e,f).
25. 8, n = 6).
26. Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A. J. Org. Chem. 1984, 49, 3928.
27. Cousseau, J. Synthesis 1980, 805.
28. Racemic 4-phenylbutylene oxide was resolved using Jacobsen's R,R-(salen)Co catalyst: Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936.
29. 3).
30. The diastereoselectivity of this reaction, and the enantiomeric purity of 7d, were identical whether (R)-5 was a 1.7:1, or 1:1.2, mixture of diastereomers. Thus, the configuration of the allylic alcohol does not affect in a detectable way the outcome of this reaction.
31. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.
32. 5 can be employed to terminate a Prins-pinacol reaction.
33. Reviews: (a) Ashby, E. C.; Laemmle, J. T. Chem. Rev. 1975, 75, 521. (b) Gung, B. W. Tetrahedron 1996, 52, 5263.
34. Reviews: (a) Ashby, E. C.; Laemmle, J. T. Chem. Rev. 1975, 75, 521. (b) Gung, B. W. Tetrahedron 1996, 52, 5263.