Abstract
Here we report the chemoenzymatic synthesis of Ro 25-8210 (1) and Ro 25-6630 (2) by using microbial reduction of α-chloromethyl ketone 4 mediated with baker’s yeast andGeotrichum sp. to afford the optically active (R) and (S)-α-chlorohydrin 8 respectively as the key step.
Similar content being viewed by others
References
Woessner, Jr. J. F., Matrix metalloproteinases and their inhibitors in connective tissue remodeling, The FASEB J., 1991, 5: 2145.
Hull, K. G., Visnick, M., Tautz., W. et al., Synthesis of Ro 25-8210 via an enantioselective oxazaborolidine-catalyzed reduction, Tetrahedron, 1997, 53(37): 12405.
Santaniello, E., Ferraboschi, P., Grisenti, P. et al., The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks, Chem. Rev., 1992, 92(5): 1071.
Csuk, R., Glanzer, B. I., Baker’s yeast mediated transformations in organic chemistry, Chem. Rev., 1991, 91(1): 49.
Wong, C. H., Whitesides, G. M., Enzymes in Synthetic Organic Chemistry, Tetrahedron Organic Chemistry Series, Vol. 12. Oxford: Pergamon, Elsevier Science Ltd., 1994.
Imuta, M., Kawai, K., Ziffer, H., Product stereospecificity in the microbial reduction of α-haloaryl ketones, J. Org. Chem., 1980, 45(16): 3352.
Wei, Z. L., Li, Z. Y., Lin, G. Q., Anti-Prelog microbial reduction of aryl α-halomethyl or α-hydroxymethyl ketones withGeotrichum sp. 38, Tetrahedron, 1998, 54: 13059.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Wei, Z., Li, Z., Lin, G. et al. Chemoenzymatic synthesis of Ro 25-8210 and Ro 25-6630. Sc. China Ser. B-Chem. 43, 331–336 (2000). https://doi.org/10.1007/BF02969529
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02969529