Design constraints in practical syntheses of complex molecules: Current status, case studies with carbohydrates and alkaloids, and future perspectives

Chemical Reviews

Volumn 96, Issue 1, 1996, Pages 3-30

  Hudlicky, Tomas ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002530666     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr950012g     Document Type: Review

References (167)

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109. As incredible as this may seem, there are some in the synthetic community that openly reject the idea of enzymatic transformations as "cheating" or the "inability to design a catalyst properly" that will accomplish turnover rates similar to those of enzymes. Some views and discourse on the possible reasons for this resistance have been published: See ref 32; Brown, S. M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, p 113; and the preface to the latter volume. Preparative biocatalysis, or the combination of enzymatic and chemical methods, has been accepted in the industrial world and in the academic communities of Europe and Japan. By comparison, very few research groups in the United States actively pursue research in this area. The resistance to accept this field is also reflected in the reluctant funding of such programs. In spite of the demonstrated superiority that biocatalytic design has over traditional methods of synthesis of enantiomerically pure compounds, research proposals dealing with preparation of medicinally viable targets by such methods have not been well received by the NIH system (in the author's experience). On the other hand, when the review of such proposals was conducted in the format used by the NSF, or by industrial pannels, the same proposals rejected by the former system were recommended by the latter. I do not believe that our case is unique in this regard, but I accept the premise that any new technology requires a transition period before it is accorded a permanent status.
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162. Three syntheses of pancratistatin or 7-deoxypancratistatin have appeared since our first-generation effort (ref 35). (a) pancratistatin: Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (b) 7-deoxypancratistatin: Keck, G. E.; Schubert, E. M.; Murry, J. A. J. Am. Chem. Soc. 1995, 117, 7289. (c) 7-deoxypancratistatin: Tian, X.; Maurya, R.; Konigsberger, K.; Hudlicky, T. Synlett 1995, 1125.
163. Three syntheses of pancratistatin or 7-deoxypancratistatin have appeared since our first-generation effort (ref 35). (a) pancratistatin: Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (b) 7-deoxypancratistatin: Keck, G. E.; Schubert, E. M.; Murry, J. A. J. Am. Chem. Soc. 1995, 117, 7289. (c) 7-deoxypancratistatin: Tian, X.; Maurya, R.; Konigsberger, K.; Hudlicky, T. Synlett 1995, 1125.
164. Three syntheses of pancratistatin or 7-deoxypancratistatin have appeared since our first-generation effort (ref 35). (a) pancratistatin: Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. (b) 7-deoxypancratistatin: Keck, G. E.; Schubert, E. M.; Murry, J. A. J. Am. Chem. Soc. 1995, 117, 7289. (c) 7-deoxypancratistatin: Tian, X.; Maurya, R.; Konigsberger, K.; Hudlicky, T. Synlett 1995, 1125.
165. Hudlicky, T.; Tian, X.; Maurya, R.; Konigsberger, K. Synlett 1995, 1125.
166. See for example: Wong, C.-H.; Whitesides, G. M. In Enzymes in Synthetic Organic Chemistry; Tetrahedron Organic Chemistry Series; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon: New York, 1994.
167. Hudlicky, T.; Maurya, R.; Thorpe, A.; Entwistle, D. A.; Bolonick, J., manuscript in preparation.