Syntheses of new phosphorus-containing azabicycloalkanes and their microbial hydroxylation using Beauveria bassiana

Journal of Organic Chemistry

Volumn 64, Issue 17, 1999, Pages 6312-6318

  Hemenway, Michael S ^a   Olivo, Horacio F ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; BICYCLO COMPOUND; PHOSPHORUS DERIVATIVE;

ARTICLE; HYDROXYLATION; MICROORGANISM; NONHUMAN; ORGANIC CHEMISTRY; SYNTHESIS;

EID: 0033588072     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9904664     Document Type: Article

References (106)

1. For reviews see: (a) Johnson, C. R.; Wells, G. W. Curr. Opin. Chem. Biol. 1998, 2, 70. (b) Roberts, S. M.; Turner, N. J.; Willetts, A. J.; Turner, M. K. Introduction to Biocatalysis Using Enzymes and Micro-Organisms; Cambridge University Press: Cambridge, 1995. (c) Johnson, R. A. Oxidation with Microorganisms. In Oxidation in Organic Chemistry; Trahanowsky, W. S., Ed.; Academic Press: New York, 1978; Vol. 50. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992. (e) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1995. (f) Jones, B. J.; Sih, G. J.; Perlman, D. Applications of Biochemical Systems in Organic Chemistry; Wiley and Sons: New York, 1976; Vol. 10. (g) Kieslich, K. Biotransformations in Biotechnology: A Comprehensive Treatise; Rehm, H. J., Reed, G., Eds.; VCH: Weinheim, 1984; Vol. 6a. (h) Furstoss, R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Enzymes as Catalysts in Organic Synthesis; Schneider, M. P., Ed.; NATO ASI Series; Reidel Dortrecht: Norwell, MA, 1986; Vol. 178, p 361. For reviews see: (a) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (b) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (c) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984. (d) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69. (e) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
2. For reviews see: (a) Johnson, C. R.; Wells, G. W. Curr. Opin. Chem. Biol. 1998, 2, 70. (b) Roberts, S. M.; Turner, N. J.; Willetts, A. J.; Turner, M. K. Introduction to Biocatalysis Using Enzymes and Micro-Organisms; Cambridge University Press: Cambridge, 1995. (c) Johnson, R. A. Oxidation with Microorganisms. In Oxidation in Organic Chemistry; Trahanowsky, W. S., Ed.; Academic Press: New York, 1978; Vol. 50. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992. (e) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1995. (f) Jones, B. J.; Sih, G. J.; Perlman, D. Applications of Biochemical Systems in Organic Chemistry; Wiley and Sons: New York, 1976; Vol. 10. (g) Kieslich, K. Biotransformations in Biotechnology: A Comprehensive Treatise; Rehm, H. J., Reed, G., Eds.; VCH: Weinheim, 1984; Vol. 6a. (h) Furstoss, R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Enzymes as Catalysts in Organic Synthesis; Schneider, M. P., Ed.; NATO ASI Series; Reidel Dortrecht: Norwell, MA, 1986; Vol. 178, p 361. For reviews see: (a) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (b) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (c) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984. (d) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69. (e) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
3. For reviews see: (a) Johnson, C. R.; Wells, G. W. Curr. Opin. Chem. Biol. 1998, 2, 70. (b) Roberts, S. M.; Turner, N. J.; Willetts, A. J.; Turner, M. K. Introduction to Biocatalysis Using Enzymes and Micro-Organisms; Cambridge University Press: Cambridge, 1995. (c) Johnson, R. A. Oxidation with Microorganisms. In Oxidation in Organic Chemistry; Trahanowsky, W. S., Ed.; Academic Press: New York, 1978; Vol. 50. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992. (e) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1995. (f) Jones, B. J.; Sih, G. J.; Perlman, D. Applications of Biochemical Systems in Organic Chemistry; Wiley and Sons: New York, 1976; Vol. 10. (g) Kieslich, K. Biotransformations in Biotechnology: A Comprehensive Treatise; Rehm, H. J., Reed, G., Eds.; VCH: Weinheim, 1984; Vol. 6a. (h) Furstoss, R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Enzymes as Catalysts in Organic Synthesis; Schneider, M. P., Ed.; NATO ASI Series; Reidel Dortrecht: Norwell, MA, 1986; Vol. 178, p 361. For reviews see: (a) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (b) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (c) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984. (d) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69. (e) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
4. For reviews see: (a) Johnson, C. R.; Wells, G. W. Curr. Opin. Chem. Biol. 1998, 2, 70. (b) Roberts, S. M.; Turner, N. J.; Willetts, A. J.; Turner, M. K. Introduction to Biocatalysis Using Enzymes and Micro-Organisms; Cambridge University Press: Cambridge, 1995. (c) Johnson, R. A. Oxidation with Microorganisms. In Oxidation in Organic Chemistry; Trahanowsky, W. S., Ed.; Academic Press: New York, 1978; Vol. 50. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992. (e) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1995. (f) Jones, B. J.; Sih, G. J.; Perlman, D. Applications of Biochemical Systems in Organic Chemistry; Wiley and Sons: New York, 1976; Vol. 10. (g) Kieslich, K. Biotransformations in Biotechnology: A Comprehensive Treatise; Rehm, H. J., Reed, G., Eds.; VCH: Weinheim, 1984; Vol. 6a. (h) Furstoss, R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Enzymes as Catalysts in Organic Synthesis; Schneider, M. P., Ed.; NATO ASI Series; Reidel Dortrecht: Norwell, MA, 1986; Vol. 178, p 361. For reviews see: (a) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (b) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (c) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984. (d) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69. (e) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
5. For reviews see: (a) Johnson, C. R.; Wells, G. W. Curr. Opin. Chem. Biol. 1998, 2, 70. (b) Roberts, S. M.; Turner, N. J.; Willetts, A. J.; Turner, M. K. Introduction to Biocatalysis Using Enzymes and Micro-Organisms; Cambridge University Press: Cambridge, 1995. (c) Johnson, R. A. Oxidation with Microorganisms. In Oxidation in Organic Chemistry; Trahanowsky, W. S., Ed.; Academic Press: New York, 1978; Vol. 50. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992. (e) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1995. (f) Jones, B. J.; Sih, G. J.; Perlman, D. Applications of Biochemical Systems in Organic Chemistry; Wiley and Sons: New York, 1976; Vol. 10. (g) Kieslich, K. Biotransformations in Biotechnology: A Comprehensive Treatise; Rehm, H. J., Reed, G., Eds.; VCH: Weinheim, 1984; Vol. 6a. (h) Furstoss, R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Enzymes as Catalysts in Organic Synthesis; Schneider, M. P., Ed.; NATO ASI Series; Reidel Dortrecht: Norwell, MA, 1986; Vol. 178, p 361. For reviews see: (a) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (b) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (c) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984. (d) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69. (e) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
6. For reviews see: (a) Johnson, C. R.; Wells, G. W. Curr. Opin. Chem. Biol. 1998, 2, 70. (b) Roberts, S. M.; Turner, N. J.; Willetts, A. J.; Turner, M. K. Introduction to Biocatalysis Using Enzymes and Micro-Organisms; Cambridge University Press: Cambridge, 1995. (c) Johnson, R. A. Oxidation with Microorganisms. In Oxidation in Organic Chemistry; Trahanowsky, W. S., Ed.; Academic Press: New York, 1978; Vol. 50. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992. (e) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1995. (f) Jones, B. J.; Sih, G. J.; Perlman, D. Applications of Biochemical Systems in Organic Chemistry; Wiley and Sons: New York, 1976; Vol. 10. (g) Kieslich, K. Biotransformations in Biotechnology: A Comprehensive Treatise; Rehm, H. J., Reed, G., Eds.; VCH: Weinheim, 1984; Vol. 6a. (h) Furstoss, R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Enzymes as Catalysts in Organic Synthesis; Schneider, M. P., Ed.; NATO ASI Series; Reidel Dortrecht: Norwell, MA, 1986; Vol. 178, p 361. For reviews see: (a) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (b) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (c) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984. (d) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69. (e) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
7. For reviews see: (a) Johnson, C. R.; Wells, G. W. Curr. Opin. Chem. Biol. 1998, 2, 70. (b) Roberts, S. M.; Turner, N. J.; Willetts, A. J.; Turner, M. K. Introduction to Biocatalysis Using Enzymes and Micro-Organisms; Cambridge University Press: Cambridge, 1995. (c) Johnson, R. A. Oxidation with Microorganisms. In Oxidation in Organic Chemistry; Trahanowsky, W. S., Ed.; Academic Press: New York, 1978; Vol. 50. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992. (e) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1995. (f) Jones, B. J.; Sih, G. J.; Perlman, D. Applications of Biochemical Systems in Organic Chemistry; Wiley and Sons: New York, 1976; Vol. 10. (g) Kieslich, K. Biotransformations in Biotechnology: A Comprehensive Treatise; Rehm, H. J., Reed, G., Eds.; VCH: Weinheim, 1984; Vol. 6a. (h) Furstoss, R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Enzymes as Catalysts in Organic Synthesis; Schneider, M. P., Ed.; NATO ASI Series; Reidel Dortrecht: Norwell, MA, 1986; Vol. 178, p 361. For reviews see: (a) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (b) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (c) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984. (d) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69. (e) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
8. For reviews see: (a) Johnson, C. R.; Wells, G. W. Curr. Opin. Chem. Biol. 1998, 2, 70. (b) Roberts, S. M.; Turner, N. J.; Willetts, A. J.; Turner, M. K. Introduction to Biocatalysis Using Enzymes and Micro-Organisms; Cambridge University Press: Cambridge, 1995. (c) Johnson, R. A. Oxidation with Microorganisms. In Oxidation in Organic Chemistry; Trahanowsky, W. S., Ed.; Academic Press: New York, 1978; Vol. 50. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992. (e) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1995. (f) Jones, B. J.; Sih, G. J.; Perlman, D. Applications of Biochemical Systems in Organic Chemistry; Wiley and Sons: New York, 1976; Vol. 10. (g) Kieslich, K. Biotransformations in Biotechnology: A Comprehensive Treatise; Rehm, H. J., Reed, G., Eds.; VCH: Weinheim, 1984; Vol. 6a. (h) Furstoss, R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Enzymes as Catalysts in Organic Synthesis; Schneider, M. P., Ed.; NATO ASI Series; Reidel Dortrecht: Norwell, MA, 1986; Vol. 178, p 361. For reviews see: (a) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (b) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (c) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984. (d) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69. (e) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
9. For reviews see: (a) Johnson, C. R.; Wells, G. W. Curr. Opin. Chem. Biol. 1998, 2, 70. (b) Roberts, S. M.; Turner, N. J.; Willetts, A. J.; Turner, M. K. Introduction to Biocatalysis Using Enzymes and Micro-Organisms; Cambridge University Press: Cambridge, 1995. (c) Johnson, R. A. Oxidation with Microorganisms. In Oxidation in Organic Chemistry; Trahanowsky, W. S., Ed.; Academic Press: New York, 1978; Vol. 50. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992. (e) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1995. (f) Jones, B. J.; Sih, G. J.; Perlman, D. Applications of Biochemical Systems in Organic Chemistry; Wiley and Sons: New York, 1976; Vol. 10. (g) Kieslich, K. Biotransformations in Biotechnology: A Comprehensive Treatise; Rehm, H. J., Reed, G., Eds.; VCH: Weinheim, 1984; Vol. 6a. (h) Furstoss, R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Enzymes as Catalysts in Organic Synthesis; Schneider, M. P., Ed.; NATO ASI Series; Reidel Dortrecht: Norwell, MA, 1986; Vol. 178, p 361. For reviews see: (a) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (b) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (c) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984. (d) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69. (e) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
10. For reviews see: (a) Johnson, C. R.; Wells, G. W. Curr. Opin. Chem. Biol. 1998, 2, 70. (b) Roberts, S. M.; Turner, N. J.; Willetts, A. J.; Turner, M. K. Introduction to Biocatalysis Using Enzymes and Micro-Organisms; Cambridge University Press: Cambridge, 1995. (c) Johnson, R. A. Oxidation with Microorganisms. In Oxidation in Organic Chemistry; Trahanowsky, W. S., Ed.; Academic Press: New York, 1978; Vol. 50. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992. (e) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1995. (f) Jones, B. J.; Sih, G. J.; Perlman, D. Applications of Biochemical Systems in Organic Chemistry; Wiley and Sons: New York, 1976; Vol. 10. (g) Kieslich, K. Biotransformations in Biotechnology: A Comprehensive Treatise; Rehm, H. J., Reed, G., Eds.; VCH: Weinheim, 1984; Vol. 6a. (h) Furstoss, R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Enzymes as Catalysts in Organic Synthesis; Schneider, M. P., Ed.; NATO ASI Series; Reidel Dortrecht: Norwell, MA, 1986; Vol. 178, p 361. For reviews see: (a) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (b) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (c) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984. (d) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69. (e) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
11. For reviews see: (a) Johnson, C. R.; Wells, G. W. Curr. Opin. Chem. Biol. 1998, 2, 70. (b) Roberts, S. M.; Turner, N. J.; Willetts, A. J.; Turner, M. K. Introduction to Biocatalysis Using Enzymes and Micro-Organisms; Cambridge University Press: Cambridge, 1995. (c) Johnson, R. A. Oxidation with Microorganisms. In Oxidation in Organic Chemistry; Trahanowsky, W. S., Ed.; Academic Press: New York, 1978; Vol. 50. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992. (e) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1995. (f) Jones, B. J.; Sih, G. J.; Perlman, D. Applications of Biochemical Systems in Organic Chemistry; Wiley and Sons: New York, 1976; Vol. 10. (g) Kieslich, K. Biotransformations in Biotechnology: A Comprehensive Treatise; Rehm, H. J., Reed, G., Eds.; VCH: Weinheim, 1984; Vol. 6a. (h) Furstoss, R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Enzymes as Catalysts in Organic Synthesis; Schneider, M. P., Ed.; NATO ASI Series; Reidel Dortrecht: Norwell, MA, 1986; Vol. 178, p 361. For reviews see: (a) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (b) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (c) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984. (d) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69. (e) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
12. For reviews see: (a) Johnson, C. R.; Wells, G. W. Curr. Opin. Chem. Biol. 1998, 2, 70. (b) Roberts, S. M.; Turner, N. J.; Willetts, A. J.; Turner, M. K. Introduction to Biocatalysis Using Enzymes and Micro-Organisms; Cambridge University Press: Cambridge, 1995. (c) Johnson, R. A. Oxidation with Microorganisms. In Oxidation in Organic Chemistry; Trahanowsky, W. S., Ed.; Academic Press: New York, 1978; Vol. 50. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992. (e) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1995. (f) Jones, B. J.; Sih, G. J.; Perlman, D. Applications of Biochemical Systems in Organic Chemistry; Wiley and Sons: New York, 1976; Vol. 10. (g) Kieslich, K. Biotransformations in Biotechnology: A Comprehensive Treatise; Rehm, H. J., Reed, G., Eds.; VCH: Weinheim, 1984; Vol. 6a. (h) Furstoss, R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Enzymes as Catalysts in Organic Synthesis; Schneider, M. P., Ed.; NATO ASI Series; Reidel Dortrecht: Norwell, MA, 1986; Vol. 178, p 361. For reviews see: (a) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (b) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (c) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984. (d) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69. (e) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
13. For reviews see: (a) Johnson, C. R.; Wells, G. W. Curr. Opin. Chem. Biol. 1998, 2, 70. (b) Roberts, S. M.; Turner, N. J.; Willetts, A. J.; Turner, M. K. Introduction to Biocatalysis Using Enzymes and Micro-Organisms; Cambridge University Press: Cambridge, 1995. (c) Johnson, R. A. Oxidation with Microorganisms. In Oxidation in Organic Chemistry; Trahanowsky, W. S., Ed.; Academic Press: New York, 1978; Vol. 50. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992. (e) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1995. (f) Jones, B. J.; Sih, G. J.; Perlman, D. Applications of Biochemical Systems in Organic Chemistry; Wiley and Sons: New York, 1976; Vol. 10. (g) Kieslich, K. Biotransformations in Biotechnology: A Comprehensive Treatise; Rehm, H. J., Reed, G., Eds.; VCH: Weinheim, 1984; Vol. 6a. (h) Furstoss, R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Enzymes as Catalysts in Organic Synthesis; Schneider, M. P., Ed.; NATO ASI Series; Reidel Dortrecht: Norwell, MA, 1986; Vol. 178, p 361. For reviews see: (a) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (b) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (c) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984. (d) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69. (e) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
14. For reviews see: (a) Johnson, C. R.; Wells, G. W. Curr. Opin. Chem. Biol. 1998, 2, 70. (b) Roberts, S. M.; Turner, N. J.; Willetts, A. J.; Turner, M. K. Introduction to Biocatalysis Using Enzymes and Micro-Organisms; Cambridge University Press: Cambridge, 1995. (c) Johnson, R. A. Oxidation with Microorganisms. In Oxidation in Organic Chemistry; Trahanowsky, W. S., Ed.; Academic Press: New York, 1978; Vol. 50. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992. (e) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1995. (f) Jones, B. J.; Sih, G. J.; Perlman, D. Applications of Biochemical Systems in Organic Chemistry; Wiley and Sons: New York, 1976; Vol. 10. (g) Kieslich, K. Biotransformations in Biotechnology: A Comprehensive Treatise; Rehm, H. J., Reed, G., Eds.; VCH: Weinheim, 1984; Vol. 6a. (h) Furstoss, R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Enzymes as Catalysts in Organic Synthesis; Schneider, M. P., Ed.; NATO ASI Series; Reidel Dortrecht: Norwell, MA, 1986; Vol. 178, p 361. For reviews see: (a) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (b) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (c) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984. (d) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69. (e) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
15. For references on epibatidine see: (a) Spande, T. F.; Garraffo, H. M.; Edwards, M. W.; Yeh, H. J. C.; Pannell, L.; Daly, J. W. J. Am. Chem. Soc. 1992, 114, 3475. (b) Fletcher, S. R; Baker, R.; Chambers, M. S.; Herbert, R. H.; Hobbs, S. C.;Thomas, S. R.; Verrier, H. M.; Watt, A. P.; Ball, R. G. J. Org. Chem. 1994, 59, 1771. (c) Szántay, C.; Kardos- Balogh, Z.; Szántay, C., Jr. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1995; Vol. 46, p 95.
16. For references on epibatidine see: (a) Spande, T. F.; Garraffo, H. M.; Edwards, M. W.; Yeh, H. J. C.; Pannell, L.; Daly, J. W. J. Am. Chem. Soc. 1992, 114, 3475. (b) Fletcher, S. R; Baker, R.; Chambers, M. S.; Herbert, R. H.; Hobbs, S. C.;Thomas, S. R.; Verrier, H. M.; Watt, A. P.; Ball, R. G. J. Org. Chem. 1994, 59, 1771. (c) Szántay, C.; Kardos- Balogh, Z.; Szántay, C., Jr. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1995; Vol. 46, p 95.
17. For references on epibatidine see: (a) Spande, T. F.; Garraffo, H. M.; Edwards, M. W.; Yeh, H. J. C.; Pannell, L.; Daly, J. W. J. Am. Chem. Soc. 1992, 114, 3475. (b) Fletcher, S. R; Baker, R.; Chambers, M. S.; Herbert, R. H.; Hobbs, S. C.;Thomas, S. R.; Verrier, H. M.; Watt, A. P.; Ball, R. G. J. Org. Chem. 1994, 59, 1771. (c) Szántay, C.; Kardos-Balogh, Z.; Szántay, C., Jr. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1995; Vol. 46, p 95.
18. (a) Fonken, G. S.; Herr, M. E.; Murray, H. C.; Reineke, L. M. J. Am. Chem. Soc. 1967, 89, 672.
19. (b) Fonken, G. S.; Herr, M. E.; Murray, H. C.; Reineke, L. M. J. Org. Chem. 1968, 33, 3182.
20. (c) Johnson, R. A.; Herr, M. E.; Murray, H. C.; Fonken, G. S. J. Org. Chem. 1968, 33, 3187.
21. (d) Johnson, R. A.; Herr, M. E.; Murray, H. C.; Reineke, L. M.; Fonken, G. S. J. Org. Chem. 1968, 33, 3195.
22. (e) Herr, M. E.; Johnson, R. A.; Murray, H. C.; Reineke, L. M.; Fonken, G. S. J. Org. Chem. 1968, 33, 3201.
23. (f) Johnson, R. A.; Murray, H. C.; Reineke, L. M.; Fonken, G. S. J. Org. Chem. 1968, 33, 3207.
24. (g) Johnson, R. A.; Herr, M. E.; Murray, H. C.; Fonken, G. S. J. Org. Chem. 1968, 33, 3217.
25. (h) Johnson, R. A.; Herr, M. E.; Murray, H. C.; Fonken, G. S. J. Org. Chem. 1970, 35, 622.
26. (i) Herr, M. E.; Johnson, R. A.; Krueger, W. C.; Murray, H. C.; Pschigoda, L. M. J. Org. Chem. 1970, 35, 3607.
27. (j) Johnson, R. A.; Herr, M. E.; Murray, H. C.; Reineke, L. J. Am. Chem. Soc. 1971, 22, 4480.
28. (k) Johnson, R. A.; Herr, M. E.; Murray, H. C.; Chidester, C. G.; Han, F. J. Org. Chem. 1992, 57, 7209.
29. (l) Johnson, R. A.; Herr, M. E.; Murray, H. C.; Krueger, W. C.; Pschigoda. L. M.; Duchamp, D. J. J. Org. Chem. 1992, 57, 7212.
30. (m) Davis, C. R.; Johnson, R. A.; Cialdella, J. I.; Liggett, W. F.; Mizsak, S. A.; Marshall, V. P. J. Org. Chem. 1997, 62, 2244.
31. (n) Davis, C. R.; Johnson, R. A.; Cialdella, J. I.; Liggett, W. F.; Mizsak, S. A.; Han, F.; Marshall, V. P. J. Org. Chem. 1997, 62, 2252.
32. (a) Holland, H. L.; Auret, B. J. Can. J. Chem. 1975, 53, 845.
33. (b) Holland, H. L.; Auret, B. J. Can. J. Chem. 1975, 53, 2041.
34. (c) Holland, H. L.; Diakow, P. R. P. Can. J. Chem. 1978, 57, 436.
35. (d) Holland, H. L.; Diakow, P. R. P. Can. J. Chem. 1979, 57, 694.
36. (e) Holland, H. L.; Diakow, P. R. P. Can. J. Chem. 1979, 57, 1585.
37. (f) Holland, H. L.; Taylor, G. J. Can. J. Chem. 1980, 58, 2326.
38. (g) Holland, H. L. Can. J. Chem. 1981, 59, 1651.
39. (h) Holland, H. L.; Taylor, G. J. Can. J. Chem. 1981, 59, 2809.
40. (i) Holland, H. L. Chem. Soc. Rev. 1982, 11, 371.
41. (j) Holland, H. L.; Thomas, E. M. Can. J. Chem. 1982, 60, 160.
42. (k) Holland, H. L. Acc. Chem. Res. 1984, 17, 398.
43. (l) Holland, H. L.; Bergen, E. J.; Chenchaiah, P. C.; Khan, S. H.; Munoz, B.; Ninniss, R. W.; Richards, D. Can. J. Chem. 1987, 65, 502.
44. (m) Holland, H. L.; Conn, M.; Chenchaiah, P. C.; Brown, F. M. Tetrahedron Lett. 1988, 29, 6393.
45. (a) Furstoss, R.; Archelas, A.; Waegell, B.; Le Petit, J.; Deveze, L. Tetrahedron Lett. 1980, 21, 451.
46. (b) Furstoss, R.; Archelas, A.; Waegell, B.; Le Petit, J.; Deveze, L. Tetrahedron Lett. 1981, 22, 445.
47. (c) Archelas, A.; Morin, C. Tetrahedron Lett. 1984, 25, 1277.
48. (d) Archelas, A.; Furstoss, R.; Waegell, B.; Le Petit, J.; Deveze, L. Tetrahedron 1984, 40, 355.
49. (e) Vigne, B.; Archelas, A.; Fourneron, J. D.; Furstoss, R. Tetrahedron 1986, 42, 2451.
50. (f) Archelas, A.; Furstoss, R.; Srairi, D.; Maury, G. Bull. Chem. Soc. Fr. 1986, 2, 234.
51. (g) Fourneron, J. D.; Archelas, A.; Vigne, B.; Furstoss, R. Tetrahedron 1987, 43, 2273.
52. (h) Vigne, B.; Archelas, A.; Fourneron, J. D.; Furstoss, R. New J. Chem. 1987, 11, 297.
53. (i) Archelas, A.; Fourneron, J.-D.; Furstoss, R.; Cesario, M.; Pascard, C. J. Org. Chem. 1988, 53, 1797.
54. (j) Fourneron, J. D.; Archelas, A.; Furstoss, R. J. Org. Chem. 1989, 54, 2478.
55. (k) Fourneron, J. D.; Archelas, A.; Furstoss, R. J. Org. Chem. 1989, 54, 4686.
56. (l) Zhang, X. M.; Archelas, A.; Furstoss, R. J. Org. Chem. 1991, 56, 3814.
57. (m) Vigne, B.; Archelas, A.; Furstoss, R. Tetrahedron 1991, 47, 1447.
58. (n) Pedragosa-Moreau, S.; Archelas, A.; Furstoss, R. J. Org. Chem. 1993, 58, 5533.
59. (a) Davies, H. G.; Dawson, M. J.; Lawrence, G. C.; Mayall, J.; Noble, D.; Roberts, S. M.; Turner, M. K.; Wall, W. F. Tetrahedron Lett. 1986, 27, 1089.
60. (b) Carruthers, W.; Prail, J. D.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc., Perkin Trans. 1 1990, 2854.
61. (c) Floyd, N.; Munyemana, F.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc., Perkin Trans. 1 1993, 881.
62. (d) Ridyard, C. H.; Whittaker, R. A.; Higgins, S. D.; Roberts, S. M.; Willetts, A. J.; Bailey, P. D.; Rosair, G. M. J. Chem. Soc., Perkin Trans. 2 1996, 1811.
63. (e) Bailey, P. D.; Higgins, S. D.; Ridyard, C. H.; Roberts, S. M.; Rosair, G. M.; Whittaker, R. A.; Willetts, A. J. Chem. Commun. 1998, 1833.
64. (f) Palmer, C. F.; Webb, B.; Broad, S.; Casson, S.; McCague, R.; Willetts, A. J.; Roberts, S. M. Bioorg. Med. Chem. Lett. 1997, 7, 1299.
65. (a) de Raadt, A.; Griengl, H.; Petsch. M.; Plachota, P.; Schoo, N.; Weber, H.; Braunegg, G.; Kopper, I.; Kreiner, M.; Zeiser, A.; Kieslich, K. Tetrahedron: Asymmetry 1996, 7, 467.
66. (b) de Raadt, A.; Griengl, H.; Petsch, M.; Plachota, P.; Schoo, N.; Weber, H.; Braunegg, G.; Kopper, I.; Kreiner, M.; Zeiser, A. Tetrahedron: Asymmetry 1996, 7, 473
67. (c) de Raadt, A.; Griengl, H.; Petsch, M.; Plachota, P.; Schoo, N.; Weber, H.; Braunegg, G.; Kopper, I.; Kreiner, M.; Zeiser, A.; Tetrahedron: Asymmetry 1996, 7, 491.
68. (d) Morwaski, B.; Griengl, H.; Ribbons, D. W.; Williams, D. J. Tetrahedron: Asymmetry 1997, 8, 845.
69. (a) Pietz, S.; Fröhlich, R.; Haufe, G. Tetrahedron 1997, 53, 17055.
70. (b) Pietz, S.; Wölker, D.; Haufe, G. Tetrahedron 1997, 53, 17067.
71. Aitken, S. J.; Grogan, G.; S.-Y. Chow, C.; Turner, N. J.; Flitsch, S. L. J. Chem. Soc., Perkin Trans. 1 1998, 3365.
72. Olivo, H. F.; Hemenway, M. S.; Gezginci, M. H. Tetrahedron Lett. 1998, 39, 1309.
73. Previously known as Sporotrichum sulfurescens and later reclassified as Beauveria sulfurescens; see: Taylor, J. J. Mycol. 1970, 62, 797. This microorganism is currently listed as Beauveria bassiana (ATCC 7159) in the catalog of the American Type Culture Collection.
74. Hill, D. L. A Review of Cyclophosphamide; Thomas: Springfield, IL, 1975.
75. Connors, T. A.; Foster, A. B.; Gilsenan, A. M.; Jarman, M.; Tisdale, M. J. Biochem. Pharmacol. 1972, 21, 1373.
76. Hassner, A.; Belostotskii, A. M. Tetrahedron Lett. 1995, 36, 1709.
77. (a) Beres, J.; Bentrude, W. G.; Parkanji, L.; Kálmán, A.; Sopchik, A. E. J. Org. Chem. 1986, 50, 1271.
78. (b) Sopchik, A. E.; Beres, J.; Tomasz, J.; Bentrude, W. G. J. Org. Chem. 1991, 56, 5911.
79. (c) Gryaznov, S.; Chen, J.-K. J. Am. Chem. Soc. 1994, 116, 3143.
80. (d) Endo, M.; Komiyama, M. J. Org. Chem. 1996, 61, 1994.
81. (e) Nelson, J. S.; Fearon, K. L.; Nguyen, M. Q.; McCurdy, S. N.; Frediani, J. E.; Foy, M. F.; Hirschbein, B. L. J. Org. Chem. 1997, 62, 7278.
82. (f) Skorski, T.; Perrotti, D.; Nieborowska-Skorska, M.; Gryaznov, S.; Calabretta, B. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 3966.
83. (g) Tereshko, V.; Gryaznov, S.; Egli, M. J. Am. Chem. Soc. 1998, 120, 269.
84. (a) Wadsworth, W. S., Jr. J. Org. Chem. 1987, 52, 1748.
85. (b) Ryu, S.; Jackson, J. A.; Thompson, C. M. J. Org. Chem. 1991, 56, 4999.
86. Fathi, R.; Rudolph, M. J.; Gentles, R. G.; Patel, R.; MacMillan, E. W.; Reitman, M. S.; Pelham, D.; Cook, A. F. J. Org. Chem. 1996, 61, 5600.
87. Zhang, Y.; Flann, C. J. J. Org. Chem. 1998, 63, 1372.
88. (a) Quin, L. D.; Szewczyk, J.; Szewczyk, K. M.; McPhail, A. T. J. Org. Chem. 1986, 51, 3341.
89. (b) Quin, L. D.; Jankowski, S. J. Org. Chem. 1994, 59, 4402.
90. (a) Gamble, M. P.; Smith, A R. C.; Wills, M. J. Org. Chem. 1998, 63, 6068.
91. (b) Gamble, M. P.; Studley, J. R.; Wills, M. Tetrahedron Lett. 1996, 37, 2853.
92. (c) Gamble, M. P.; Studley, J. R.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 3071.
93. (d) Burns, B.; Gamble, M. P.; Smith, A. R. C.; Studley, J. R.; Alcock, N. W.; Wills, M. Tetrahedron: Asymmetry 1997, 8, 73.
94. (a) Zwierzak, A. Synthesis 1975, 507.
95. (b) Sabesan, S.; Neira, S. Carbohydr. Res. 1992, 223, 169.
96. (c) Mora, N.; Lacombe, J. M.; Pavia, A. A. Tetrahedron Lett. 1993, 34, 2461.
97. (a) Wolfrom, M. L.; Conigliaro, P. J.; Soltes, E. J. J. Org. Chem. 1967, 32, 653.
98. (b) Kenner, G. W.; Moore, G. A.; Ramage, R. Tetrahedron Lett. 1976, 40, 3623.
99. (c) Zhao, Y.-F.; Xi, S.-K.; Song, A.-T.; Ji, G.-J. J. Org. Chem. 1984, 49, 4549.
100. (d) Zwierzak, A. Osowska, K. Synthesis 1984, 223.
101. (e) Dudash, J., Jr.; Jiang, J.; Mayer, S. C.; Joullié, M. M. Synth. Commun. 1993, 23, 349.
102. We were unable to isolate hydroxylated metabolites when the free amine 7-azabicyclo[2.2.1]heptane was subjected to cultures of B. bassiana following our biotransformation protocol.
103. Furstoss, R.; Archelas, A.; Fourneron, J. D.; Vigne, B. Biohydroxylation of nonactivated carbon atoms by fungus Beauveria sulferescens. In Organic Synthesis - An Interdisciplinary Challenge; Streith, J., Prinzbach, H., Schill, G., Eds.; Blackwell: Oxford, 1985; p 215.
104. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
105. (a) Ramage, R.; Hopton, D.; Parrott, M. J.; Kenner, G. W.; Moore, G. A. J. Chem. Soc., Perkin Trans. 1 1984, 1357.
106. (b) Ramage, R.; Atrash, B.; Hopton, D.; Parrott, M. J. J. Chem. Soc., Perkin Trans. 1 1985, 1217.