Enzymes in Action pp 433-448 | Cite as
Application of Enzymes in Synthetic Strategy
Chapter
Abstract
The use of enzymes in organic synthesis is now commonly accepted. The earlier reluctance that these sensitive bioreagents would not withstand the reaction conditions normally employed in organic synthesis has fainted. The organic chemists amazingly quickly learned how to adjust the experimental conditions of synthetic operations allowing the fruitful use of enzymes. In addition, it was shown that enzymes can be used in organic solvents as well. Furthermore, many new methodologies have been developed for the directed use of enzymes in synthetic conversions.
Keywords
Vinyl Acetate Kinetic Resolution Carboxylic Ester Stereogenic Center Enantioselective Hydrolysis
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References
- 1.Wong, C.H. and Whitesides, G.M. (1994) Enzymes in synthetic organic chemistry, Pergamon Press (Tetrahedron Series vol 12); Faber, K. (1995) Biotransformations in organic chemistry, Springer-Verlag, Berlin (2ndEd.).Google Scholar
- 2.Gastel, F.J.C. van, Klunder, A.J.H. and Zwanenburg, B. (1988) unpublished results. See also: Gastel, F.J.C. van (1992) Enzymatic optical resolution of norbornene-type carboxylic esters and their application in synthesisThesisUniversity of Nymegen, The Netherlands.Google Scholar
- 3.Dumont, M., Klunder, A.J.H. and Zwanenburg, B. (1984) unpublished results.Google Scholar
- 4.Smeets, F.L.M. and Zwanenburg, B. (1981) unpublished results. See also: Smeets, F.L.M. (1981) Synthese van pyrenophorineThesisUniversity of Nymegen, The Netherlands. For colletallol: Legters, J., Thijs, L. and Zwanenburg, B. (1985) unpublished results.Google Scholar
- 5.Gastel, F.J.C. van, Klunder, A.J.H. and Zwanenburg, B. (1992) unpublished results. See also ref. 2.Google Scholar
- 6.Klunder, A.J.H., Bos, W., Verlaak, J.M.J. and Zwanenburg, B. (1981) A facile synthesis of functionalized cyclopentadienone epoxides by flash vacuum thermolytic cycloreversion of tricyclodecenonesTetrahedron Lett.4553–4556.Google Scholar
- 7.Klunder, A.J.H., Bos, W. and Zwanenburg, B. (1981) An efficient stereospecific total synthesis of (–)terreinTetrahedron Lett.4557–4560.Google Scholar
- 8.Klunder, A.J.H., Zhu, J. and Zwanenburg, B. (1999) The concept of transient chirality in the stereoselective synthesis of functionalized cycloalkenes applying the retro Diels-Alder methodologyChem. Rev.99, 1163–1190.CrossRefGoogle Scholar
- 9.Zwanenburg, B., Zhu, J. and Klunder, A.J.H. (1997) Cyclopentenoid natural products inNew Horizon in Organic SynthesisEds. Nair, V. and Kumar, S., New Age International Publ., New Delhi, India.Google Scholar
- 10.Klunder, A.J.H., Valk, W.C.G.M. de, Verlaak, J.M.J., Schellekens, J.W.M., Noordik, J.H., Parthasarathi, V. and Zwanenburg, B. (1985) Nucleophilic eliminative ring fission of bridgehead substituted 1,3-bishomocubyl acetatesTetrahedron 41 963–973.CrossRefGoogle Scholar
- 11.Klunder, A.J.H., Huizinga, W.B., Hulshof, A.J.M. and Zwanenburg, B. (1986) Enzymatic optical resolution and absolute configuration of tricyclo[5.2.1.02’6]decadienonesTetrahedron Lett.27 25432546.Google Scholar
- 12.Klunder, A.J.H., Huizinga, W.B., Sessink, P.J.M. and Zwanenburg, B. (1987) Enzymatic optical resolution and flash vacuum thermolysis in concert for the synthesis of optically active cyclopentenonesTetrahedron Lett.28 357–360.CrossRefGoogle Scholar
- 13.Zhu, J., Yang, J.-Y., Klunder, A.J.H., Liu, Z.-Y. and Zwanenburg, B. (1995) A stereo-and enantioselective approach to clavulones from tricyclodecadienone using flash vacuum thermolysisTetrahedron 51 5847–5870.CrossRefGoogle Scholar
- 14.Takano, S., Inomata, K. And Ogasawara, K. (1989) Enantioconvergent route to a-cuparenone from dicyclopentadieneJ. Chem. Soc.Chem. Commun.271.Google Scholar
- 15.Liu, Z.-Y., He, L. and Zheng, H. (1993) Highly enantioselective synthesis of (+) and (-)endotricyclo[5.2.1.0 2 • 6 ]deca-4 8-dien-3-one by enzyme catalysed acetylationTetrahedron Asymm. 4 2277.CrossRefGoogle Scholar
- 16.Bakkeren, F.J.A.D., Ramesh, N.G., Groot, D. De, Klunder, A.J.H. and Zwanenburg, B. (1996) Asymmetric desymmetrization of a pseudo-meso-endo-tricyclo[5.2.1.02•6]deca-4,8-dien-3-one by chiral aminesTetrahedron Lett.37 8003–8006.CrossRefGoogle Scholar
- 17.Mohr, P., Waespe-arcevic, N., Tamm, C., Gawronska, K. and Gawronski, J.K. (1983)Heiv. Chim. Acta66, 2501.CrossRefGoogle Scholar
- 18.Klunder, A.J.H., Gastel, F.J.C. van, and Zwanenburg, B. (1988) Structural requirements in the enzymatic optical resolution of bicyclic esters using Pig Liver EsteraseTetrahedron Lett.2926972700. Gastel, F.J.C. van, Klunder, A.J.H., and Zwanenburg, B. (1991) Enzymatic optical resolution of norbornene carboxylic esters using Pig Liver EsteraseRecl. Tray. Chim. Pays-Bas 110175–184.Google Scholar
- 19.Wigchert, S.C.M. and Zwanenburg, B. (1999) A critical account on the interception ofStrigaseed germination,J. Agric. Food. Chem.471320–1325 and literature cited therein.CrossRefGoogle Scholar
- 20.Thuring, J.W.J.F., Nefkens, G.H.L., Schaafstra, R. and Zwanenburg, B. (1995) Asymmetric synthesis of a D-ring synthon for strigol analogues and its application to the synthesis of all four diastereo-isomers of germination stimulant GR7Tetrahedron 51 5047–5056.CrossRefGoogle Scholar
- 21.Thuring, J.W.J.F., Klunder, A.J.H., Nefkens, G.H.L., Wegman, M.A. and Zwanenburg, B. (1996) Enzymatic kinetic resolution of 5-hydroxy-4-oxa-endo-tricyclo[5.2.1.026]deca-4,8-dien-3-ones: a useful approach to D-ring synthons for strigol analogues with remarkable stereoselectivityJ. Org . Chem.61 6931–6935.CrossRefGoogle Scholar
- 22.Sugimoto, Y., Wigchert, S.C.M., Thuring, J.W.J.F. and Zwanenburg, B. (1998) Synthesis of all eight stereoisomers of the germination stimulant sorgolactoneJ. Org . Chem.63 1259–1267 and references cited therein.Google Scholar
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