A Model For Predicting Diastereoselectivity In Yeast Reductions

References

• Bolte J., Gourey J., Veschambre H. Utilisation des methodes biologiques pour la preparation de synthons chiraux: I-reduction de β-dicetones acycliques par. Saccharomyces cerevisiae (Levure de Boulaner). Tetrahedron Lett. 1986; 27: 565–568
   Google Scholar
• Brooks D., Mazdiyasni H., Salley P. Microbial reduction of prochiral 2, 2-disubstituted 1, 3-cycloheheptanediones. J. Org. Chem. 1985; 50: 3411–3414
   Google Scholar
• Chen C. S., Zhou B. N., Girdaukas G., Shieh W., VanMiddlesworth R., Gopalan F. A.S., Sih C. J. Stereochemical control of yeast reductions. 2. Quantitative treatment of the kinetics of competing enzyme systems for a single substrate. Biorg. Chem. 1984; 12: 98–117
   Google Scholar
• Deol B., Ridley D., Simpson G. Asymmetric reduction of carbonyl compounds by yeast. II. Preparation of optically active α and β-hydroxy carboxylic acid derivatives. Aus. J. Chem. 1976; 29: 2459–2967
   Web of Science ®Google Scholar
• DeShong P., Lin M., Perez J. Total synthesis of the (+)-pheromone of the male swift moth. Hepialus hecta L. Tetrahedron Lett. 1986; 27: 2091–2094
   Google Scholar
• Frater G., Muller U., Gunther W. The stereoselective α-alkylation of chiral β-hydroxy esters and some applications thereof. Tetrahedron. 1984; 40: 1269–1277
   Web of Science ®Google Scholar
• Fuganti C., Grasselli P. On the steric course of baker's yeast mediated reduction of alkyl 4-azido- and 4-bromo-3-oxobutyrate. Synthesis of. (R)- and (S)-carnitin. Tetrahedron Lett. 1985; 26: 101–104
   Web of Science ®Google Scholar
• Fujisawa T., Itoh T., Sato T. Enantiospecific synthesis of optically pure (3S)-hydroxy esters by the stereocontrolled yeast reduction of α-sulfenyl-β-ketoesters. Tetrahedron Lett. 1984; 25: 5083–5086
   Web of Science ®Google Scholar
• Fujisawa T., Kojima E., Itoh T., Sato T. Diastereo- and enantioselective reduction of α, β-diketodithiane with the baker's yeast. Tetrahedron Lett. 1985; 26: 6089–6092
   Web of Science ®Google Scholar
• Furuichi A., Akita H., Matsukura H., Oishi T., Horikoshi K. Purification and properties of an asymmetric reduction enzyme of 2-methyl-3-oxobutyrate in baker's yeast. Agric. Biol. Chem. 1985; 49: 2563–2570
   Web of Science ®Google Scholar
• Hirama M., Shimizu M., Iwashita M. Enantiospecific syntheses of trifunctional (R)-3–hydroxy esters by baker's yeast reduction. J. Chem. Soc. Chem. Commun. 1983; 599
   Google Scholar
• Hirama M., Nakamine T., Ito S. Trifunctional chiral synthons via stereocontrolled yeast reduction. Preparation of chiral pentane-1.3.5-triol derivatives. Chem. Lett. 1986; 1381: 1384
   Google Scholar
• Hoffmann R., Helbig W., Ladner W. Synthesis of 6S,7S-anhydro-serricornine. Tetrahedron Lett. 1982; 3479–3482
   Google Scholar
• Kieslich K. Microbial Transformations of Non-Steroid Cyclic Compounds. Georg Thieme Verlag, Stuttgart 1976
   Google Scholar
• Kitahara T., Mori K. preparation of chiral cyclohexanol derivative with high optical purity by yeast reduction. Tetrahedron Lett. 1985; 26: 451–452
   Google Scholar
• Lieser J. A simple synthesis of (S, S)-2,5-hexanediol. Synth. Commun. 1983; 13: 765–767
   Web of Science ®Google Scholar
• McLeod R., Prosser H., Fikentscher L., Lanyi J., Mosher H. S. Asymmetric reductions. XII. Stereoselective ketone reductions by fermenting yeast. Biochemistry 1964; 3: 838
   Google Scholar
• Mori K., Mori H., Sugai T. Biochemical preparations of both the enantiomers of methyl 3-hydroxypentanoate and their conversion to the enantiomers of 4-hexanolide, the pheromone of. Trogoderma glabrum. Tetrahedron 1985; 41: 919–925
   Web of Science ®Google Scholar
• Mori K., Mori H., Yanai M. Synthesis of (2S,4aS,8aR)-(-)-1,1,4a-trimethyl-2-decalol, an inhibitor of steroid biosynthesis. Tetrahedron 1986; 42: 291–294
   Google Scholar
• Nakamura K., Ushio K., Oka S., Ohno A. Stereochemical control in yeast reduction. Tetrahedron Lett. 1984; 25: 3979–3982
   Web of Science ®Google Scholar
• Nakamura K., Higaki M., Ushio K., Oka S., Ohno A. Stereochemical control of microbial reduction. 2. Reduction of -keto esters by immobilized baker's yeast. Tetrahedron Lett. 1985; 26: 4213–4216
   Web of Science ®Google Scholar
• Nakamura K., Miyai T., Nozaki K., Ushio K., Oka S., Ohno A. Diastereo- and enantioselective reduction of 2-methyl-3-oxobutanoate by baker's yeast. Tetrahedron Lett. 1986; 27: 3155–3156
   Web of Science ®Google Scholar
• Neuberg C., Lewite A. XIV. Hydrogenation of a ketone by yeast. Transformation of methylheptenone into methylheptenol. Biochem. Z. 1918; 91: 257–266
   Google Scholar
• Prelog V. Specification of the stereospecificity of some oxidoreductases by diamond lattice sections. Pure Appl. Chem. 1984; 9: 119–130
   Google Scholar
• Sato T., Tsurumaki M., Fujisawa T. Enantioselective synthesis of (2S,3S)-2,3–dihydroxyalkanoates by the baker's yeast reduction of 2-hydroxy-3-oxoalkanoates. Chem. Lett. 1986; 1367–1370
   Google Scholar
• Seebach D., Sutter M., Weber R., Zuger M. Yeast reduction of ethyl acetoacetate: (S) – (+)-ethyl 3-hydroxybutanoate. Organic Syntheses 1984; 63: 1–9
   Google Scholar
• Shieh W. R., Gopalan A. S., Sih C. J. Stereochemical control of yeast reductions. 5. Characterization of the oxidoreductases involved in the reduction of β-keto esters. J. Am. Chem. Soc. 1985; 107: 2993–2994
   Web of Science ®Google Scholar
• Sih C. J., Rosazza J. P. Microbial transformations in organic synthesis. Applications of Biochemical Systems in Organic Chemistry, Part I, J. B. Jones, C. J. Sih, D. Perlman. Wiley, New York 1976; Chapter III: 69–106
   Google Scholar
• Sih C. J., Zhou B. N., Gopalan A. S., Shieh W. R., VanMiddlesworth F. Strategies for controlling the stereochemical course of yeast reductions. Selectivity-A Goal for Synthetic Efficiency, Workshop Conference Hoechst, W. Bartmann, B. Trost. Verlag Chemie., Weinheim 1983; Vol. 14: 251–261
   Google Scholar
• Sih C. J., Chen C. S. Microbial asymmetric catalysis-enantioselective reduction of ketones. Angew. Chem. Int. Ed. Engl. 1984; 23: 570–578
   Web of Science ®Google Scholar
• Tsuboi S., Nishiyama E., Utaka M., Takeda A. A facile synthesis of (R)-(-)- hexahydromandelic acid with fermenting baker's yeast. Tetrahedron Lett. 1986; 27: 1915–1916
   Web of Science ®Google Scholar
• Ushio K., Inouye K., Nakamura K., Oka S., Ohno A. Stereochemical control in microbial reduction. 4. Effect of cultivation conditions on the reduction of β-keto esters by methylotrophic yeasts. Tetrahedron Lett. 1986; 27: 2657–2660
   Google Scholar
• Wipf B., Kupfer E., Bertazzi R., Leuenberger H. Production of (+)-S-ethyl 3–hydroxybutyrate and (-)–(R)-ethyl 3-hydroxybutyrate by microbial reduction of ethyl acetoacetate. Helv. Chim. Acta 1983; 66: 485–488
   Web of Science ®Google Scholar
• Zhou B. N., Gopalan A. S., VanMiddlesworth F., Shieh W. R., Sih C. J. Stereochemical control of yeast reductions. 1. Asymmetric synthesis of 1-carnitine. J. Am. Chem. Soc. 1983; 105: 5925–5926
   Web of Science ®Google Scholar