Enantioselective synthesis of (R)-(-)-mevalonolactone via cyclic sulfate methodology

Tetrahedron Asymmetry

Volumn 10, Issue 22, 1999, Pages 4349-4356

  Fernandes, Rodney A ^a   Kumar, Pradeep ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; MEVALONOLACTONE; SULFATE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; ENANTIOMER; HYDROXYLATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0033370214     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00496-6     Document Type: Article

References (50)

1. For reviews concerning the discovery and role of mevalonolactone, see: (a) Goldstein, J. L.; Brown, M. S. Nature 1990, 343, 425-430. (b) Herbert, R. B. The Biosynthesis of Secondary Metabolites, 2nd ed.; Chapman and Hall: London, 1989. (c) Caspi, E. Tetrahedron 1986, 42, 3-50. (d) Goodwin, T. W. Natural Substances Formed Biologically from Mevalonic Acid; Academic Press: New York, 1970; pp. 45-47.
2. For reviews concerning the discovery and role of mevalonolactone, see: (a) Goldstein, J. L.; Brown, M. S. Nature 1990, 343, 425-430. (b) Herbert, R. B. The Biosynthesis of Secondary Metabolites, 2nd ed.; Chapman and Hall: London, 1989. (c) Caspi, E. Tetrahedron 1986, 42, 3-50. (d) Goodwin, T. W. Natural Substances Formed Biologically from Mevalonic Acid; Academic Press: New York, 1970; pp. 45-47.
3. For reviews concerning the discovery and role of mevalonolactone, see: (a) Goldstein, J. L.; Brown, M. S. Nature 1990, 343, 425-430. (b) Herbert, R. B. The Biosynthesis of Secondary Metabolites, 2nd ed.; Chapman and Hall: London, 1989. (c) Caspi, E. Tetrahedron 1986, 42, 3-50. (d) Goodwin, T. W. Natural Substances Formed Biologically from Mevalonic Acid; Academic Press: New York, 1970; pp. 45-47.
4. For reviews concerning the discovery and role of mevalonolactone, see: (a) Goldstein, J. L.; Brown, M. S. Nature 1990, 343, 425-430. (b) Herbert, R. B. The Biosynthesis of Secondary Metabolites, 2nd ed.; Chapman and Hall: London, 1989. (c) Caspi, E. Tetrahedron 1986, 42, 3-50. (d) Goodwin, T. W. Natural Substances Formed Biologically from Mevalonic Acid; Academic Press: New York, 1970; pp. 45-47.
5. (a) Kumar, P.; Saravanan, K. Tetrahedron 1998, 54, 2161-2168.
6. (b) Pais, G. C. G.; Fernandes, R. A.; Kumar, P. Tetrahedron 1999, 55, 13445-13450.
7. (c) Pais, G. C. G. Ph.D. Thesis, National Chemical Laboratory, Pune, India, 1997.
8. (a) Folkers, K.; Shunk, C. H.; Linn, B. O.; Robinson, F. M.; Wittreich, P. E.; Huff, J. W.; Gilfillan, J. L.; Skeggs, H. R. Discovery and Elucidation of Mevalonic Acid in Ciba Foundation Symposium on the Biosynthesis of Terpenes and Sterols; Wolstenholme, G. E. W.; O'Connor, M., Eds.; J. S. A. Churchill Ltd: London, 1959; pp. 20-43.
9. (a) Ray, N. C.; Raveendranath, P. C.; Spencer, T. A. Tetrahedron 1992, 48, 9427-9432.
10. (b) Bolitt, V.; Mioskowski, C.; Bhatt, R. K.; Falck, J. R. J. Org. Chem. 1991, 56, 4238-4240.
11. (c) Ohta, T.; Tabei, N.; Nozoe, S. Heterocycles 1989, 28, 425-432.
12. (d) Schneider, J. A.; Yoshihara, K. J. Org. Chem. 1986, 51, 1077-1079.
13. (e) Mori, K.; Okada, K. Tetrahedron 1985, 41, 557-559.
14. (f) Bonadies, F.; Rossi, G.; Bonini, C. Tetrahedron Lett. 1984, 25, 5431-5434.
15. (a) Wilson, W. K.; Scallen, T. J.; Morrow, C. J. J. Lipid Res. 1982, 23, 645-652.
16. (b) Cornforth, R. H.; Cornforth, J. W.; Popjak, G. Tetrahedron 1962, 18, 1351-1354.
17. Eberle, M.; Arigoni, D. Helv. Chim. Acta 1960, 43, 1508-1513.
18. Davis, F. A.; Reddy, G. V.; Chen, B. C.; Kumar, A.; Haque, M. S. J. Org. Chem. 1995, 60, 6148-6153.
19. Shimizu, M.; Kamikubo, T.; Ogasawara, K. Tetrahedron: Asymmetry 1997, 8, 2519-2521.
20. Kishida, M.; Yamauchi, N.; Sawada, K.; Ohashi, Y.; Eguchi, T.; Kakinuma, K. J. Chem. Soc., Perkin Trans 1 1997, 891-895.
21. Abushanab, E.; Reed, D.; Suzuki, F.; Sih, C. J. Tetrahedron Lett. 1978, 3415-3418.
22. (a) Frye, S. V.; Eliel, E. L. Tetrahedron Lett. 1986, 3223-3226.
23. (b) Frye, S. V.; Eliel, E. L. J. Am. Chem. Soc. 1988, 110, 484-489.
24. Kawakami, Y.; Hiratake, J.; Yamamoto, Y.; Oda, J. J. Chem. Soc., Chem. Commun. 1984, 779-781.
25. (a) Orru, R. V. A.; Osprian, I.; Kroutil, W.; Faber, K. Synthesis 1998, 1259-1263.
26. (b) Lakher, F. J.; Hager, L. P. J. Org. Chem. 1996, 61, 3923-3925.
27. (c) Ferraboschosi, P.; Grisenti, P.; Casati, S.; Santaniello, E. Synlett 1994, 754-756.
28. (d) Sugai, T.; Kakeya, H.; Ohta, H. Tetrahedron 1990, 46, 3463-3468.
29. (e) Francis, C. J.; Jones, J. B. J. Chem. Soc., Chem. Commun. 1984, 579-580.
30. (f) Ohta, H.; Tetsukawa, H.; Noto, N. J. Org. Chem. 1982, 47, 2400-2404.
31. (g) Irwin, A. J.; Jones, J. B. J. Am. Chem. Soc. 1977, 99, 556-561.
32. (h) Huang, F. C.; Lee, L. F. H.; Mittal, R. S. D.; Ravikumar, P. R.; Chan, J. A.; Sih, C. J.; Caspi, E.; Eck, C. R. J. Am. Chem. Soc. 1975, 97, 4144-4145.
33. Eliel, E. L.; Soai, K. Tetrahedron Lett. 1981, 30, 2859-2862.
34. 3-Methyl-3-butene-1-o1 was procured from Aldrich Chemical Company.
35. (a) Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 448-451.
36. (b) Torii, S.; Liu, P.; Bhuvaneswari, N.; Amatore, C.; Jutand, A. J. Org. Chem. 1996, 61, 3055-3060.
37. (c) Corey, E. J.; Guzman-Perez, A.; Noe, M. C. Tetrahedron Lett. 1995, 36, 3481-3484.
38. (d) Tietze, L. F.; Golitzer, J. Synthesis 1998, 873-878.
39. (e) For a review on the asymmetric dihydroxylation, see: Kolb, H. C.; VanNiewenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
40. For the measurement of enantiomeric excess, the diol 3 was converted into the triol 9. The enantiomeric purity of the triol 9 was estimated to be in excess of 89% by GLC using Chirasil-Val-D (25 m×0.32 mm I.D.) at 120°C for 5 min, 10°C/min to 220°C. (Matrix Presented)
41. For a review on cyclic sulfites and sulfates, see: Lohray, B. B. Synthesis 1992, 1035-1052.
42. For the synthesis of cyclic sulfates from diols containing acid sensitive groups and chemoselective hydrolysis of sulfate esters, see: Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655-658.
43. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
44. Frye, S. V.; Eliel, E. L. J. Org. Chem. 1985, 50, 3402-3404.
45. Gu, J.-X.; Holland, H. L. Synth. Commun. 1998, 28, 3305-3315.
46. (a) Nangia, A.; Madusudan Rao, B.; Prasuna, G. Synth. Commun. 1992, 22, 593-602.
47. (b) Bonadies, F.; Di Fabio, R. J. Org. Chem. 1984, 49, 1647-1649.
48. (c) Herold, P.; Mohr, P.; Tamm, C. Helv. Chim. Acta 1983, 66, 744-754.
49. (d) White, J. D.; Carter, J. P.; Kazar III, H. S. J. Org. Chem. 1982, 47, 929-932.
50. Noyori, R.; Ohkuma, T.; Kitamura, M. J. Am. Chem. Soc. 1987, 109, 5856-5858 and references cited therein.