Toward a ‘reagent-free’ synthesis

Abstract

Several synthetic pathways to cyclohex-5-ene-1R,2S,3R,4R-tetrol (conduritol C) and cyclohex-5-ene-1S,2R,3R,4R-tetrol (conduritol F) are compared; each is analyzed for effectiveness of waste minimization. The latest synthesis, reported in this manuscript, combines enzymatic transformations with electrochemical methods. The concept of “effective mass yield” (EMY) is defined and illustrated.

References

1. T. Hudlicky, Chem. Rev., 1996, 96, 3.
2. P. A. Wender and B. L. Miller, Organic Synthesis: Theory and Applications, ed. T. Hudlicky, JAI Press, Greenwich, CT, 1993, vol. 2, pp. 27–66.
3. R. A. Sheldon, Chemtech, 1994, 38.
4. R. A. Sheldon, Chem. Ind., 1997, 12.
5. B. M. Trost, Science, 1991, 254, 1470.
6. R. A. Sheldon, Chem. Ind., 1992, 903.
7. S. M. Weinreb and M. C. McIntosh, J. Org. Chem., 1993, 58, 4823.
8. T. Hudlicky, H. Luna and H. F. Olivo, J. Chem. Soc., Perkin Trans. I, 1991, 2907.
9. T. Hudlicky, R. Fan, T. Tsunoda and H. Luna, Isr. J. Chem., 1991, 31, 229.
10. T. Hudlicky, C. D. Claeboe, L. E. Brammer Jr., L. Koroniak and I. GhivirigaJ. Org. Chem., 1999, submitted..
11. (a) For toxicity and pollution limits for these solvents see: K. Verschueren, Handbook of Environmental Data on Organic Chemicals, Van Nostrand Reinhold, New York, 1983; (b) P. H. Howard, Handbook of Enviromental Fate and Exposure Data for Organic Chemicals, Lewis Publishers, Chelsea, MI, 1990.
12. (a) For comprehensive reviews of arene cis-diol chemistry see: S. M. Brown and T. Hudlicky, Organic Synthesis: Theory and Applications, ed. T. Hudlicky, JAI Press, Greenwich, CT, 1993, vol. 2, pp. 113–176; (b) D. A. Widdowson, D. W. Ribbons and S. D. Thomas, Janssen Chim. Acta, 1990, 8, 3; (c) H. A. J. Carless, Tetrahedron: Asymmetry., 1992, 3, 795; (d) T. Hudlicky and J. W. Reed, Advances in Asymmetric Synthesis, ed. A. Hassner, JAI Press, Greenwich, CT, 1995, pp. 271–312; (e) T. Hudlicky, Green Chemistry: Designing Chemistry for the Environment, ACS Symp. Ser. 626, ed. P. T. Anastas and T. C. Williamson, American Chemical Society, Washington, DC, 1996, ch. 14; (f) T. Hudlicky and J. Thorpe, Chem Commun., 1996, 1993; (g) T. Hudlicky, Chem. Rev., 1996, 96, 3; (h) T. Hudlicky, D. A. Entwistle, K. K. Pitzer and A. J. Thorpe, Chem. Rev., 1996, 96, 1195; (i) A. D. Grund, SIM News, 1995, 45, 59; (j) D. R. Boyd, Nat. Prod. Rep., 1998, 309; (k) T. Hudlicky, D. Gonzalez and D. T. Gibson, Aldrichim. Acta, 1999, in press..
13. (a) G. Majetich, R. Hicks, G. Sun and P. McGill, J. Org. Chem., 1998, 63, 2564; (b) G. Majetich and R. Hicks, Synlett, 1996, 649.
14. All calculations are shown in tabular form in the Supplementary Material, (see footnote †).