Enantioselective synthesis of 5-substituted α,β-unsaturated δ- lactones: Application to the synthesis of styryllactones

Tetrahedron Letters

Volumn 41, Issue 2, 2000, Pages 183-187

  Harris, Joel M ^a   O'Doherty, George A ^a  

^a University of Minnesota ^*  (United States)

Author keywords

Asymmetric synthesis; Carbohydrates; Lactones; Sharpless dihydroxylation

Indexed keywords

CARBOHYDRATE; LACTONE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034620205     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02050-X     Document Type: Article

References (44)

1. (a) Yasui, K.; Tamura, Y.; Nakatani, T.; Kawada, K.; Ohtani, M. J. Org. Chem. 1995, 60, 7567-7574 and references cited therein.
2. (b) Fang, X.-P.; Anderson, J. E.; Chang, C.-J.; McLaughlin, J. L.; Fanwick, P. E. J. Nat. Prod. 1991, 54, 1034.
3. (c) Argoudelis, A. D.; Zieserl, J. F. Tetrahedron Lett. 1966, 18, 1969.
4. (d) For a review of 5,6-dihydro-2H-pyran-2-ones, see: Davies-Coleman, M. T.; Rivett, D. E. A. In Progress in the Chemistry of Organic Natural Products; Herz, W.; Grisebach, H.; Kirby, G. W.; Tamm, Ch., Eds.; Springer-Verlag: New York, 1989; Vol. 55, pp. 1-35.
5. (a) Schlessing, R. H.; Gillman, K. W. Tetrahedron Lett. 1999, 40, 1257-1260.
6. (b) Tsubuki, M.; Kanai, K.; Nagase, H.; Honda, T. Tetrahedron 1999, 55, 2493-2514.
7. (c) Chen, W.-P.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1999, 103-105.
8. (d) Dixon, D. J.; Ley, S. V.; Tate, E. W. J. Chem. Soc., Perkin Trans. 1 1998, 3125-3126.
9. (e) Yang, Z.-C.; Jiang, X.-B.; Wang, Z.-M; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 317-321.
10. (f) Gomez, A. M.; Lopez de Uralde, B.; Valverde, S.; Lopez, J. C. Chem. Commun. 1997, 1647.
11. (g) Honda, T.; Sano, N.; Kanai, K. Heterocycles 1995, 41, 425-429.
12. (h) Yang, Z.-C.; Zhou, W.-S. Tetrahedron Lett. 1995, 36, 5617-5618.
13. (i) Masaki, Y.; Imaeda, T.; Oda, H.; Itoh, A.; Shiro, M. Chem. Lett. 1992, 1209-1212.
14. For a review, see: (j) Ogliaruso, M. A.; Wolfe, J. F. In Synthesis of Lactones and Lactams; Patai, S.; Rappoport, Z., Eds.; John Wiley & Sons: New York, 1993; pp. 3-131; 271-396.
15. (a) Kametani, T.; Tsubuki, M.; Tatsuzaki, Y.; Honda, T. Heterocycles 1988, 27, 2107-2110.
16. (b) Kametani, T.; Tsubuki, M.; Tatsuzaki, Y.; Honda, T. J. Chem. Soc., Perkin Trans. 1 1990, 639-646.
17. (c) Honda, T.; Kametani, T.; Kanai, K.; Tatsuzaki, Y.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1990, 1733-1737.
18. (a) Kobayashi, Y.; Kusakabe, M.; Kitano, Y.; Sato, F. J. Org. Chem. 1988, 53, 1587-1590.
19. (b) Kusakabe, M.; Kitano, Y.; Kobayashi, Y.; Sato, F. J. Org. Chem. 1989, 54, 2085-2091.
20. (a) Yang, Z.-C.; Zhou, W.-S. Tetrahedron Lett. 1995, 36, 5617-5618.
21. (b) Yang, Z.-C.; Jiang, X.-B.; Wang, Z.-M.; Zhou, W.-S. J. Chem. Soc., Chem. Commun. 1995, 2389.
22. (c) see Ref. 2e.
23. Harris, J. M.; Keranen, M. D.; O'Doherty, G. A. J. Org. Chem. 1999, 64, 2982-2983.
24. (a) Taniguchi, T.; Nakamura, K.; Ogasawara, K. Synlett 1996, 971.
25. (b) Taniguchi, T.; Ohnishi, H.; Ogasawara, K. Chem. Commun. 1996, 1477-1478.
26. For a review, see: (c) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
27. 19F NMR of the Mosher ester derivative.
28. (a) Grapsas, I.; Couladouros, E. A.; Georgiadis, M. P. Pol. J. Chem. 1990, 64, 823.
29. (b) Georgiadis, M. P.; Couladoros, E. A. J. Org. Chem. 1986, 51, 2725-2727.
30. Luche, J.-L. J. Am. Chem. Soc. 1978, 110, 2226.
31. The absolute and relative stereochemistry of 9a and 9b were determined by correlation to our previous syntheses of a protected gulose and talose whose stereochemistry were determined by X-ray crystal analysis, see Ref. 6.
32. (a) Kuo, Y.-H.; Shih, K.-S. Heterocycles 1990, 31, 1941-1949.
33. (b) Tsubuki, M.; Kanai, K.; Honda, T. J. Chem. Soc., Chem. Commun. 1992, 1640-1641.
34. (c) Zhou, W.-S.; Yang, Z.-C. Tetrahedron Lett. 1993, 34, 7075-7076.
35. (d) see Refs. 2e, 2h.
36. Ketolactone 10 decomposed when attempting to purify by silica gel chromatography.
37. 4Si: C, 56.23; H, 7.87. Found: C, 56.10; H, 7.68.
38. 4Si: C, 55.79; H, 8.59. Found: C, 55.63; H, 8.45.
39. Various selectivities have been observed depending on the steric bulk of the substituent at C-5. (a) Honda, T.; Takada, H.; Miki, S.; Tsubuki, M. Tetrahedron Lett. 1993, 34, 8275-8278. (b) Tsubuki, M.; Takada, H.; Katoh, T.; Miki, S.; Honda, T. Tetrahedron 1996, 52, 14515-14532. (c) see Refs. 2e, 5a, 11a-c.
40. Various selectivities have been observed depending on the steric bulk of the substituent at C-5. (a) Honda, T.; Takada, H.; Miki, S.; Tsubuki, M. Tetrahedron Lett. 1993, 34, 8275-8278. (b) Tsubuki, M.; Takada, H.; Katoh, T.; Miki, S.; Honda, T. Tetrahedron 1996, 52, 14515-14532. (c) see Refs. 2e, 5a, 11a-c.
41. Various selectivities have been observed depending on the steric bulk of the substituent at C-5. (a) Honda, T.; Takada, H.; Miki, S.; Tsubuki, M. Tetrahedron Lett. 1993, 34, 8275-8278. (b) Tsubuki, M.; Takada, H.; Katoh, T.; Miki, S.; Honda, T. Tetrahedron 1996, 52, 14515-14532. (c) see Refs. 2e, 5a, 11a-c.
42. 13C NMR, FTIR, HRMS, and EA analysis.
43. 4Si: C, 55.79; H, 8.59. Found: C, 55.61; H, 8.59.
44. Mitsunobu, O. Synthesis 1981, 1.