Diacetone-glucose architecture as a chirality template. Part 9.¹ Enantioselective synthesis of (R)-mevalonolactone and (R)-[²H₉]mevalonolactone on carbohydrate template

Abstract

A highly enantioselective synthetic methodology for (R)-mevalonolactone has been developed based upon the chirality-transcription approach using a chiral template, diacetone-D-glucos-3-ulose 2. (R)-Mevalonolactone 1a is prepared from ketone 2 in 5 steps in 11% overall yield. This methodology is further applied to the synthesis of fully deuteriated (R)-[²H₉]mevalonolactone 1b starting from ketone 2 and methyl [²H₇]senecioate 7.

References

1. Part 8, Y. Maeda, K. Tago, T. Eguchi and K. Kakinuma, Biosci. Biotechnol. Biochem., 1996, 60, 1248.
2. J. R. Hanson, in Comprehensive Organic Chemistry, ed. E. Haslam, Pergamon Press, Oxford, 1979, vol. 5, p. 989; G. Britton, in Compehensive Organic Chemistry, ed. E. Haslam, Pergamon Press, Oxford, 1979, vol. 5, p. 1025.
3. M. H. Beale, Nat. Prod. Rep., 1991, 8, 441; D. M. Harrison, Nat. Prod. Rep., 1990, 7, 459.
4. I. R. Rüegg, J. Würsch, K. F. Gey and A. Pletscher, Helv. Chim. Acta, 1957, 40, 2369; J. W. Cornforth, Tetrahedron, 1959, 5, 311; W. F. Gray, G. L. Deets and T. Cohen, J. Org. Chem., 1968, 33, 4532; A. I. Scott, G. T. Phillips, P. B. Reichardt and J. G. Sweeny, J. Chem. Soc., Chem. Commun., 1970, 1396; M. Seiler, W. Acklin and D. Arigoni, J. Chem. Soc., Chem. Commun., 1970, 1394; J. W. Cornforth and F. P. Ross, J. Chem. Soc., Chem. Commun., 1970, 1395; H. G. Fross, M. Tcheng-Lin, C.-J. Chang, B. Naidoo, G. E. Blair, C. I. Abou-Chaar and J. M. Cassady, J. Am. Chem. Soc., 1974, 96, 1898; D. E. Cane and R. E. Levin, J. Am. Chem. Soc., 1976, 98, 1183; A. I. Scott and K. Shishido, J. Chem. Soc., Chem. Commun., 1980, 400.
5. R. H. Cornforth, J. W. Cornforth and G. Popjak, Tetrahedron, 1962, 18, 1351.
6. P. Blattmann and J. Rétey, J. Chem. Soc., Chem. Commun., 1970, 139; F.-C. Huang, L. F. H. Lee, R. S. D. Mittal, P. R. Ravikumar, J. A. Chan and C. J. Sih, J. Am. Chem. Soc., 1975, 97, 4144; E. L. Eliel, K. Soai and W. R. Kenan, Tetrahedron Lett., 1981, 22, 2859; Y. Kawakami, J. Hiratake, Y. Yamamoto and J. Oda, J. Chem. Soc., Chem. Commun., 1984, 779; F. Bonadies, G. Rossi and C. Bonini, Tetrahedron Lett., 1984, 25, 5431; S. V. Frye and E. L. Eliel, J. Org. Chem., 1985, 50, 3402; K. Mori and K. Okada, Tetrahedron, 1985, 41, 557; K. Fuji, M. Node and M. Murata, Tetrahedron Lett., 1986, 27, 5381; J. Hiratake, M. Inagaki, Y. Yamamoto and J. Oda, J. Chem. Soc., Perkin Trans. 1, 1987, 1053; S. Takano, Y. Shimazaki and K. Ogasawara, Heterocycles, 1990, 31, 917; T. Sugai, H. Kakeya and H. Ohta, Tetrahedron, 1990, 46, 3463; E. A. Mash and J. B. Arterburn, J. Org. Chem., 1991, 56, 885; N. C. Ray, P. C. Raveendranath and T. A. Spencer, Tetrahedron, 1992, 48, 9427; F. A. Davis, G. V. Reddy, B.-C. Chen, A. Kumar and M. S. Haque, J. Org. Chem., 1995, 60, 6148.
7. K. Kakinuma, N. Imamura and Y. Saba, Tetrahedron Lett., 1982, 23, 1697.
8. K. Kobayashi, H. G. Floss and K. Kakinuma, J. Org. Chem, 1984, 49, 1290.
9. K. Kakinuma, Y. Iihama, I. Takagi, K. Ozawa, N. Yamauchi, N. Imamura, Y. Esumi and M. Uramoto, Tetrahedron, 1992, 48, 3763.
10. T. Eguchi, T. Koudate and K. Kakinuma, Tetrahedron, 1993, 49, 4527.
11. K. Kakinuma and H.-Y. Li, Tetrahedron Lett., 1989, 30, 4157; K. Kakinuma, H. Terasawa, H.-Y. Li, K. Miyazaki and T. Oshima, Biosci. Biotechnol. Biochem., 1993, 57, 1916.
12. M. Kishida, T. Eguchi and K. Kakinuma, Tetrahedron Lett., 1996, 37, 2061.
13. U. Burkert and N. L. Allinger, in Molecular Mechanics, The American Chemical Society, Washington, DC, 1982.
14. A. J. H. Labuschagne and D. F. Schneider, Tetrahedron Lett., 1983, 24, 743.
15. Molecular Structure Corporation, 3304 Longmire Drive, College Station, TX 77840, USA, 1987.
16. G. M. Sheldrick, SHELXL93, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1993.