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Volumn 65, Issue 1, 2000, Pages 129-135

Access to Wieland-Miescher ketone in an enantiomerically pure form by a kinetic resolution with yeast-mediated reduction

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

EID: 0033963525     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991192n     Document Type: Article
Times cited : (54)

References (55)
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    • Harada, N.1    Sugioka, T.2    Ando, Y.3    Uda, H.4    Kuriki, T.5
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    • For recent examples from (R)-1, see the folllowing. (+)-Halenaquinol: Harada, N.; Sugioka, T.; Ando, Y.; Uda, H.; Kuriki, T. J. Am. Chem. Soc. 1988, 110, 8483-8487. (-)-Chaparrinone: Grieco, P. A.; Collins, J. L.; Moher, E. D.; Fleck, T. J.; Gross, R. S. J. Am. Chem. Soc. 1993, 115, 6078-6093. (+)-Grinderic acid: Paquette, L. A.; Wang, H.-L. J. Org. Chem. 1996, 61, 5352-5357. (-)-O-Methylshikoccin: Paquette, L. A.; Backhaus, D.; Braun, R.; Underiner, T. L.; Fuchs, K. J. Am. Chem. Soc. 1997, 119, 9662-9671. For recent examples from (S)-1, see the following. (+)-Paspalicine: Smith, A. B., III; Kingery- Wood, J.; Leenay, T. L.; Nolen, E. G.; Sunazuka, T. J. Am. Chem. Soc. 1992, 114, 1438-1449. (+)-Pyripyropene: A, Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Omura, S. J. Org. Chem. 1995, 60, 8126-8127. Paclitaxel: Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. J. J. Am. Chem. Soc. 1996, 118, 2843-2859. (+)- Avarol: An, J.; Wiemer, D. F. J. Org. Chem. 1996, 61, 8775-8779. (+)-Labd-8(17)-ene-3β,15-diol: Pemp, A.; Seifert, K. Tetrahedron Lett. 1997, 38, 2081-2084.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 6078-6093
    • Grieco, P.A.1    Collins, J.L.2    Moher, E.D.3    Fleck, T.J.4    Gross, R.S.5
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    • For recent examples from (R)-1, see the folllowing. (+)-Halenaquinol: Harada, N.; Sugioka, T.; Ando, Y.; Uda, H.; Kuriki, T. J. Am. Chem. Soc. 1988, 110, 8483-8487. (-)-Chaparrinone: Grieco, P. A.; Collins, J. L.; Moher, E. D.; Fleck, T. J.; Gross, R. S. J. Am. Chem. Soc. 1993, 115, 6078-6093. (+)-Grinderic acid: Paquette, L. A.; Wang, H.-L. J. Org. Chem. 1996, 61, 5352-5357. (-)-O-Methylshikoccin: Paquette, L. A.; Backhaus, D.; Braun, R.; Underiner, T. L.; Fuchs, K. J. Am. Chem. Soc. 1997, 119, 9662-9671. For recent examples from (S)-1, see the following. (+)-Paspalicine: Smith, A. B., III; Kingery- Wood, J.; Leenay, T. L.; Nolen, E. G.; Sunazuka, T. J. Am. Chem. Soc. 1992, 114, 1438-1449. (+)-Pyripyropene: A, Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Omura, S. J. Org. Chem. 1995, 60, 8126-8127. Paclitaxel: Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. J. J. Am. Chem. Soc. 1996, 118, 2843-2859. (+)- Avarol: An, J.; Wiemer, D. F. J. Org. Chem. 1996, 61, 8775-8779. (+)-Labd-8(17)-ene-3β,15-diol: Pemp, A.; Seifert, K. Tetrahedron Lett. 1997, 38, 2081-2084.
    • (1996) J. Org. Chem. , vol.61 , pp. 5352-5357
    • Paquette, L.A.1    Wang, H.-L.2
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    • 0030691768 scopus 로고    scopus 로고
    • For recent examples from (R)-1, see the folllowing. (+)-Halenaquinol: Harada, N.; Sugioka, T.; Ando, Y.; Uda, H.; Kuriki, T. J. Am. Chem. Soc. 1988, 110, 8483-8487. (-)-Chaparrinone: Grieco, P. A.; Collins, J. L.; Moher, E. D.; Fleck, T. J.; Gross, R. S. J. Am. Chem. Soc. 1993, 115, 6078-6093. (+)-Grinderic acid: Paquette, L. A.; Wang, H.-L. J. Org. Chem. 1996, 61, 5352-5357. (-)-O-Methylshikoccin: Paquette, L. A.; Backhaus, D.; Braun, R.; Underiner, T. L.; Fuchs, K. J. Am. Chem. Soc. 1997, 119, 9662-9671. For recent examples from (S)-1, see the following. (+)-Paspalicine: Smith, A. B., III; Kingery- Wood, J.; Leenay, T. L.; Nolen, E. G.; Sunazuka, T. J. Am. Chem. Soc. 1992, 114, 1438-1449. (+)-Pyripyropene: A, Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Omura, S. J. Org. Chem. 1995, 60, 8126-8127. Paclitaxel: Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. J. J. Am. Chem. Soc. 1996, 118, 2843-2859. (+)- Avarol: An, J.; Wiemer, D. F. J. Org. Chem. 1996, 61, 8775-8779. (+)-Labd-8(17)-ene-3β,15-diol: Pemp, A.; Seifert, K. Tetrahedron Lett. 1997, 38, 2081-2084.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 9662-9671
    • Paquette, L.A.1    Backhaus, D.2    Braun, R.3    Underiner, T.L.4    Fuchs, K.5
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    • 0000096617 scopus 로고
    • For recent examples from (R)-1, see the folllowing. (+)-Halenaquinol: Harada, N.; Sugioka, T.; Ando, Y.; Uda, H.; Kuriki, T. J. Am. Chem. Soc. 1988, 110, 8483-8487. (-)-Chaparrinone: Grieco, P. A.; Collins, J. L.; Moher, E. D.; Fleck, T. J.; Gross, R. S. J. Am. Chem. Soc. 1993, 115, 6078-6093. (+)-Grinderic acid: Paquette, L. A.; Wang, H.-L. J. Org. Chem. 1996, 61, 5352-5357. (-)-O-Methylshikoccin: Paquette, L. A.; Backhaus, D.; Braun, R.; Underiner, T. L.; Fuchs, K. J. Am. Chem. Soc. 1997, 119, 9662-9671. For recent examples from (S)-1, see the following. (+)-Paspalicine: Smith, A. B., III; Kingery-Wood, J.; Leenay, T. L.; Nolen, E. G.; Sunazuka, T. J. Am. Chem. Soc. 1992, 114, 1438-1449. (+)-Pyripyropene: A, Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Omura, S. J. Org. Chem. 1995, 60, 8126-8127. Paclitaxel: Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. J. J. Am. Chem. Soc. 1996, 118, 2843-2859. (+)- Avarol: An, J.; Wiemer, D. F. J. Org. Chem. 1996, 61, 8775-8779. (+)-Labd-8(17)-ene-3β,15-diol: Pemp, A.; Seifert, K. Tetrahedron Lett. 1997, 38, 2081-2084.
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    • Smith A.B. III1    Kingery-Wood, J.2    Leenay, T.L.3    Nolen, E.G.4    Sunazuka, T.5
  • 7
    • 0029556699 scopus 로고
    • For recent examples from (R)-1, see the folllowing. (+)-Halenaquinol: Harada, N.; Sugioka, T.; Ando, Y.; Uda, H.; Kuriki, T. J. Am. Chem. Soc. 1988, 110, 8483-8487. (-)-Chaparrinone: Grieco, P. A.; Collins, J. L.; Moher, E. D.; Fleck, T. J.; Gross, R. S. J. Am. Chem. Soc. 1993, 115, 6078-6093. (+)-Grinderic acid: Paquette, L. A.; Wang, H.-L. J. Org. Chem. 1996, 61, 5352-5357. (-)-O-Methylshikoccin: Paquette, L. A.; Backhaus, D.; Braun, R.; Underiner, T. L.; Fuchs, K. J. Am. Chem. Soc. 1997, 119, 9662-9671. For recent examples from (S)-1, see the following. (+)-Paspalicine: Smith, A. B., III; Kingery- Wood, J.; Leenay, T. L.; Nolen, E. G.; Sunazuka, T. J. Am. Chem. Soc. 1992, 114, 1438-1449. (+)-Pyripyropene: A, Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Omura, S. J. Org. Chem. 1995, 60, 8126-8127. Paclitaxel: Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. J. J. Am. Chem. Soc. 1996, 118, 2843-2859. (+)- Avarol: An, J.; Wiemer, D. F. J. Org. Chem. 1996, 61, 8775-8779. (+)-Labd-8(17)-ene-3β,15-diol: Pemp, A.; Seifert, K. Tetrahedron Lett. 1997, 38, 2081-2084.
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    • Nagamitsu, T.A.1    Sunazuka, T.2    Obata, R.3    Tomoda, H.4    Tanaka, H.5    Harigaya, Y.6    Omura, S.7
  • 8
    • 11044223276 scopus 로고    scopus 로고
    • For recent examples from (R)-1, see the folllowing. (+)-Halenaquinol: Harada, N.; Sugioka, T.; Ando, Y.; Uda, H.; Kuriki, T. J. Am. Chem. Soc. 1988, 110, 8483-8487. (-)-Chaparrinone: Grieco, P. A.; Collins, J. L.; Moher, E. D.; Fleck, T. J.; Gross, R. S. J. Am. Chem. Soc. 1993, 115, 6078-6093. (+)-Grinderic acid: Paquette, L. A.; Wang, H.-L. J. Org. Chem. 1996, 61, 5352-5357. (-)-O-Methylshikoccin: Paquette, L. A.; Backhaus, D.; Braun, R.; Underiner, T. L.; Fuchs, K. J. Am. Chem. Soc. 1997, 119, 9662-9671. For recent examples from (S)-1, see the following. (+)-Paspalicine: Smith, A. B., III; Kingery- Wood, J.; Leenay, T. L.; Nolen, E. G.; Sunazuka, T. J. Am. Chem. Soc. 1992, 114, 1438-1449. (+)-Pyripyropene: A, Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Omura, S. J. Org. Chem. 1995, 60, 8126-8127. Paclitaxel: Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. J. J. Am. Chem. Soc. 1996, 118, 2843-2859. (+)- Avarol: An, J.; Wiemer, D. F. J. Org. Chem. 1996, 61, 8775-8779. (+)-Labd-8(17)-ene-3β,15-diol: Pemp, A.; Seifert, K. Tetrahedron Lett. 1997, 38, 2081-2084.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 2843-2859
    • Danishefsky, S.J.1    Masters, J.J.2    Young, W.B.3    Link, J.T.4    Snyder, L.B.5    Magee, T.V.6    Jung, D.K.7    Isaacs, R.C.A.8    Bornmann, W.G.9    Alaimo, C.A.10    Coburn, C.A.11    Di Grandi, M.J.12
  • 9
    • 0030443456 scopus 로고    scopus 로고
    • For recent examples from (R)-1, see the folllowing. (+)-Halenaquinol: Harada, N.; Sugioka, T.; Ando, Y.; Uda, H.; Kuriki, T. J. Am. Chem. Soc. 1988, 110, 8483-8487. (-)-Chaparrinone: Grieco, P. A.; Collins, J. L.; Moher, E. D.; Fleck, T. J.; Gross, R. S. J. Am. Chem. Soc. 1993, 115, 6078-6093. (+)-Grinderic acid: Paquette, L. A.; Wang, H.-L. J. Org. Chem. 1996, 61, 5352-5357. (-)-O-Methylshikoccin: Paquette, L. A.; Backhaus, D.; Braun, R.; Underiner, T. L.; Fuchs, K. J. Am. Chem. Soc. 1997, 119, 9662-9671. For recent examples from (S)-1, see the following. (+)-Paspalicine: Smith, A. B., III; Kingery- Wood, J.; Leenay, T. L.; Nolen, E. G.; Sunazuka, T. J. Am. Chem. Soc. 1992, 114, 1438-1449. (+)-Pyripyropene: A, Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Omura, S. J. Org. Chem. 1995, 60, 8126-8127. Paclitaxel: Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. J. J. Am. Chem. Soc. 1996, 118, 2843-2859. (+)-Avarol: An, J.; Wiemer, D. F. J. Org. Chem. 1996, 61, 8775-8779. (+)-Labd-8(17)-ene-3β,15-diol: Pemp, A.; Seifert, K. Tetrahedron Lett. 1997, 38, 2081-2084.
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    • This yeast strain was isolated from soil and identified by Deutsche Sammlung von Mikroorganismen und Zellikulturen GbmH (DSMZ). It was deposited at the Institute for Fermentation, Osaka (IFO), and now available from this Institute, 2-17-85 Juso-honmachi, Yodogawa-ku, Osaka 532-8686, Japan. For details, see the Experimental Section
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