Chemoenzymatic taxanes approach using both enantiomers of the same building block. 2. Taxol CD ring unit

Journal of Organic Chemistry

Volumn 70, Issue 9, 2005, Pages 3484-3489

  Uttaro, Jean Pierre ^a   Audran, Gérard ^a   Monti, Honoré ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CONSTRUCTION; ENZYMES; SYNTHESIS (CHEMICAL);

BUILDING BLOCKS; CHEMOENZYMATIC TAXANES APPROACH; CHIRAL CENTERS; ENANTIOMERS;

ORGANIC POLYMERS;

DOCETAXEL; PACLITAXEL; TAXANE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; STEREOCHEMISTRY; SYNTHESIS;

CATALYSIS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PACLITAXEL; STEREOISOMERISM; TAXOIDS;

EID: 17844373308     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050039s     Document Type: Article

References (75)

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44. Reviews for biocatalytic strategies which lead to the formation of a single enantiomer in 100% theorical yield from a racemate: (a) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36. (b) Stecher, H.; Faber, K. Synthesis 1997, 1. (c) Stürmer, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1173. (d) Persson, B. A.; Larsson, A. L. E.; Le Ray, M.; Bäckvall, J.-E. J. Am. Chem. Soc. 1999, 121, 1645. (e) El Gihani, M. T.; Williams, J. M. J. Biocatal. Biotransform. 1999, 3, 11. (f) Strauss, U. T.; Felfer, U.; Faber, K. Tetrahedron: Asymmetry 1999, 10, 107.
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47. Syntheses of the fully functionalized Taxol CD ring unit: (a) Magee, T. V.; Bornmann, W. G.; Isaacs, R. C. A.; Danishefsky, S. J. J. Org. Chem. 1992, 57, 3274. (b) Nicolaou, K. C.; Liu, J. J.; Hwang, C.-K.; Dai, W.-M.; Guy, R. K. J. Chem. Soc., Chem. Commun. 1992, 1118. (c) Isaacs, R. C. A.; Di Grandi, M. J.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 3938. (d) Takahashi, T.; Hirose, Y.; Iwamoto, H.; Doi, T. J. Org. Chem. 1998, 63, 5742. (e) Nakada, M.; Kojima, E.-I.; Iwata, Y. Tetrahedron Lett. 1998, 39, 313. (f) Momose, T., Setoguchi, M.; Fujita, T.; Tamura, H.; Chida, N. Chem. Commun. 2000, 2237. (g) Nakai, K.; Miyamoto, S.; Sasuga, D.; Doi, T.; Takahashi, T. Tetrahedron Lett. 2001, 42, 7859. (h) Yoshimitsu, T.; Nakajima, H.; Nagaoka, H. Tetrahedron Lett. 2002, 43, 8587. (i) Shing, T. K. M.; Lee, C. M.; Lo, H. Y. Tetrahedron 2004, 60, 9179. Construction of the oxetane D ring in semisyntheses of taxanes which lacked functionality at C-7. (j) Potier's original procedure applied in numerous diversified methodologies: Ettovani, L.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1991, 47, 9823. (k) Zeng, Q.; Paquette, L. A. Synlett 1999, 1547. (l) Paquette, L. A.; Lo, H. Y. J. Org. Chem. 2003, 68, 2282.
48. Syntheses of the fully functionalized Taxol CD ring unit: (a) Magee, T. V.; Bornmann, W. G.; Isaacs, R. C. A.; Danishefsky, S. J. J. Org. Chem. 1992, 57, 3274. (b) Nicolaou, K. C.; Liu, J. J.; Hwang, C.-K.; Dai, W.-M.; Guy, R. K. J. Chem. Soc., Chem. Commun. 1992, 1118. (c) Isaacs, R. C. A.; Di Grandi, M. J.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 3938. (d) Takahashi, T.; Hirose, Y.; Iwamoto, H.; Doi, T. J. Org. Chem. 1998, 63, 5742. (e) Nakada, M.; Kojima, E.-I.; Iwata, Y. Tetrahedron Lett. 1998, 39, 313. (f) Momose, T., Setoguchi, M.; Fujita, T.; Tamura, H.; Chida, N. Chem. Commun. 2000, 2237. (g) Nakai, K.; Miyamoto, S.; Sasuga, D.; Doi, T.; Takahashi, T. Tetrahedron Lett. 2001, 42, 7859. (h) Yoshimitsu, T.; Nakajima, H.; Nagaoka, H. Tetrahedron Lett. 2002, 43, 8587. (i) Shing, T. K. M.; Lee, C. M.; Lo, H. Y. Tetrahedron 2004, 60, 9179. Construction of the oxetane D ring in semisyntheses of taxanes which lacked functionality at C-7. (j) Potier's original procedure applied in numerous diversified methodologies: Ettovani, L.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1991, 47, 9823. (k) Zeng, Q.; Paquette, L. A. Synlett 1999, 1547. (l) Paquette, L. A.; Lo, H. Y. J. Org. Chem. 2003, 68, 2282.
49. Syntheses of the fully functionalized Taxol CD ring unit: (a) Magee, T. V.; Bornmann, W. G.; Isaacs, R. C. A.; Danishefsky, S. J. J. Org. Chem. 1992, 57, 3274. (b) Nicolaou, K. C.; Liu, J. J.; Hwang, C.-K.; Dai, W.-M.; Guy, R. K. J. Chem. Soc., Chem. Commun. 1992, 1118. (c) Isaacs, R. C. A.; Di Grandi, M. J.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 3938. (d) Takahashi, T.; Hirose, Y.; Iwamoto, H.; Doi, T. J. Org. Chem. 1998, 63, 5742. (e) Nakada, M.; Kojima, E.-I.; Iwata, Y. Tetrahedron Lett. 1998, 39, 313. (f) Momose, T., Setoguchi, M.; Fujita, T.; Tamura, H.; Chida, N. Chem. Commun. 2000, 2237. (g) Nakai, K.; Miyamoto, S.; Sasuga, D.; Doi, T.; Takahashi, T. Tetrahedron Lett. 2001, 42, 7859. (h) Yoshimitsu, T.; Nakajima, H.; Nagaoka, H. Tetrahedron Lett. 2002, 43, 8587. (i) Shing, T. K. M.; Lee, C. M.; Lo, H. Y. Tetrahedron 2004, 60, 9179. Construction of the oxetane D ring in semisyntheses of taxanes which lacked functionality at C-7. (j) Potier's original procedure applied in numerous diversified methodologies: Ettovani, L.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1991, 47, 9823. (k) Zeng, Q.; Paquette, L. A. Synlett 1999, 1547. (l) Paquette, L. A.; Lo, H. Y. J. Org. Chem. 2003, 68, 2282.
50. Syntheses of the fully functionalized Taxol CD ring unit: (a) Magee, T. V.; Bornmann, W. G.; Isaacs, R. C. A.; Danishefsky, S. J. J. Org. Chem. 1992, 57, 3274. (b) Nicolaou, K. C.; Liu, J. J.; Hwang, C.-K.; Dai, W.-M.; Guy, R. K. J. Chem. Soc., Chem. Commun. 1992, 1118. (c) Isaacs, R. C. A.; Di Grandi, M. J.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 3938. (d) Takahashi, T.; Hirose, Y.; Iwamoto, H.; Doi, T. J. Org. Chem. 1998, 63, 5742. (e) Nakada, M.; Kojima, E.-I.; Iwata, Y. Tetrahedron Lett. 1998, 39, 313. (f) Momose, T., Setoguchi, M.; Fujita, T.; Tamura, H.; Chida, N. Chem. Commun. 2000, 2237. (g) Nakai, K.; Miyamoto, S.; Sasuga, D.; Doi, T.; Takahashi, T. Tetrahedron Lett. 2001, 42, 7859. (h) Yoshimitsu, T.; Nakajima, H.; Nagaoka, H. Tetrahedron Lett. 2002, 43, 8587. (i) Shing, T. K. M.; Lee, C. M.; Lo, H. Y. Tetrahedron 2004, 60, 9179. Construction of the oxetane D ring in semisyntheses of taxanes which lacked functionality at C-7. (j) Potier's original procedure applied in numerous diversified methodologies: Ettovani, L.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1991, 47, 9823. (k) Zeng, Q.; Paquette, L. A. Synlett 1999, 1547. (l) Paquette, L. A.; Lo, H. Y. J. Org. Chem. 2003, 68, 2282.
51. Syntheses of the fully functionalized Taxol CD ring unit: (a) Magee, T. V.; Bornmann, W. G.; Isaacs, R. C. A.; Danishefsky, S. J. J. Org. Chem. 1992, 57, 3274. (b) Nicolaou, K. C.; Liu, J. J.; Hwang, C.-K.; Dai, W.-M.; Guy, R. K. J. Chem. Soc., Chem. Commun. 1992, 1118. (c) Isaacs, R. C. A.; Di Grandi, M. J.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 3938. (d) Takahashi, T.; Hirose, Y.; Iwamoto, H.; Doi, T. J. Org. Chem. 1998, 63, 5742. (e) Nakada, M.; Kojima, E.-I.; Iwata, Y. Tetrahedron Lett. 1998, 39, 313. (f) Momose, T., Setoguchi, M.; Fujita, T.; Tamura, H.; Chida, N. Chem. Commun. 2000, 2237. (g) Nakai, K.; Miyamoto, S.; Sasuga, D.; Doi, T.; Takahashi, T. Tetrahedron Lett. 2001, 42, 7859. (h) Yoshimitsu, T.; Nakajima, H.; Nagaoka, H. Tetrahedron Lett. 2002, 43, 8587. (i) Shing, T. K. M.; Lee, C. M.; Lo, H. Y. Tetrahedron 2004, 60, 9179. Construction of the oxetane D ring in semisyntheses of taxanes which lacked functionality at C-7. (j) Potier's original procedure applied in numerous diversified methodologies: Ettovani, L.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1991, 47, 9823. (k) Zeng, Q.; Paquette, L. A. Synlett 1999, 1547. (l) Paquette, L. A.; Lo, H. Y. J. Org. Chem. 2003, 68, 2282.
52. Syntheses of the fully functionalized Taxol CD ring unit: (a) Magee, T. V.; Bornmann, W. G.; Isaacs, R. C. A.; Danishefsky, S. J. J. Org. Chem. 1992, 57, 3274. (b) Nicolaou, K. C.; Liu, J. J.; Hwang, C.-K.; Dai, W.-M.; Guy, R. K. J. Chem. Soc., Chem. Commun. 1992, 1118. (c) Isaacs, R. C. A.; Di Grandi, M. J.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 3938. (d) Takahashi, T.; Hirose, Y.; Iwamoto, H.; Doi, T. J. Org. Chem. 1998, 63, 5742. (e) Nakada, M.; Kojima, E.-I.; Iwata, Y. Tetrahedron Lett. 1998, 39, 313. (f) Momose, T., Setoguchi, M.; Fujita, T.; Tamura, H.; Chida, N. Chem. Commun. 2000, 2237. (g) Nakai, K.; Miyamoto, S.; Sasuga, D.; Doi, T.; Takahashi, T. Tetrahedron Lett. 2001, 42, 7859. (h) Yoshimitsu, T.; Nakajima, H.; Nagaoka, H. Tetrahedron Lett. 2002, 43, 8587. (i) Shing, T. K. M.; Lee, C. M.; Lo, H. Y. Tetrahedron 2004, 60, 9179. Construction of the oxetane D ring in semisyntheses of taxanes which lacked functionality at C-7. (j) Potier's original procedure applied in numerous diversified methodologies: Ettovani, L.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1991, 47, 9823. (k) Zeng, Q.; Paquette, L. A. Synlett 1999, 1547. (l) Paquette, L. A.; Lo, H. Y. J. Org. Chem. 2003, 68, 2282.
53. Syntheses of the fully functionalized Taxol CD ring unit: (a) Magee, T. V.; Bornmann, W. G.; Isaacs, R. C. A.; Danishefsky, S. J. J. Org. Chem. 1992, 57, 3274. (b) Nicolaou, K. C.; Liu, J. J.; Hwang, C.-K.; Dai, W.-M.; Guy, R. K. J. Chem. Soc., Chem. Commun. 1992, 1118. (c) Isaacs, R. C. A.; Di Grandi, M. J.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 3938. (d) Takahashi, T.; Hirose, Y.; Iwamoto, H.; Doi, T. J. Org. Chem. 1998, 63, 5742. (e) Nakada, M.; Kojima, E.-I.; Iwata, Y. Tetrahedron Lett. 1998, 39, 313. (f) Momose, T., Setoguchi, M.; Fujita, T.; Tamura, H.; Chida, N. Chem. Commun. 2000, 2237. (g) Nakai, K.; Miyamoto, S.; Sasuga, D.; Doi, T.; Takahashi, T. Tetrahedron Lett. 2001, 42, 7859. (h) Yoshimitsu, T.; Nakajima, H.; Nagaoka, H. Tetrahedron Lett. 2002, 43, 8587. (i) Shing, T. K. M.; Lee, C. M.; Lo, H. Y. Tetrahedron 2004, 60, 9179. Construction of the oxetane D ring in semisyntheses of taxanes which lacked functionality at C-7. (j) Potier's original procedure applied in numerous diversified methodologies: Ettovani, L.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1991, 47, 9823. (k) Zeng, Q.; Paquette, L. A. Synlett 1999, 1547. (l) Paquette, L. A.; Lo, H. Y. J. Org. Chem. 2003, 68, 2282.
54. Syntheses of the fully functionalized Taxol CD ring unit: (a) Magee, T. V.; Bornmann, W. G.; Isaacs, R. C. A.; Danishefsky, S. J. J. Org. Chem. 1992, 57, 3274. (b) Nicolaou, K. C.; Liu, J. J.; Hwang, C.-K.; Dai, W.-M.; Guy, R. K. J. Chem. Soc., Chem. Commun. 1992, 1118. (c) Isaacs, R. C. A.; Di Grandi, M. J.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 3938. (d) Takahashi, T.; Hirose, Y.; Iwamoto, H.; Doi, T. J. Org. Chem. 1998, 63, 5742. (e) Nakada, M.; Kojima, E.-I.; Iwata, Y. Tetrahedron Lett. 1998, 39, 313. (f) Momose, T., Setoguchi, M.; Fujita, T.; Tamura, H.; Chida, N. Chem. Commun. 2000, 2237. (g) Nakai, K.; Miyamoto, S.; Sasuga, D.; Doi, T.; Takahashi, T. Tetrahedron Lett. 2001, 42, 7859. (h) Yoshimitsu, T.; Nakajima, H.; Nagaoka, H. Tetrahedron Lett. 2002, 43, 8587. (i) Shing, T. K. M.; Lee, C. M.; Lo, H. Y. Tetrahedron 2004, 60, 9179. Construction of the oxetane D ring in semisyntheses of taxanes which lacked functionality at C-7. (j) Potier's original procedure applied in numerous diversified methodologies: Ettovani, L.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1991, 47, 9823. (k) Zeng, Q.; Paquette, L. A. Synlett 1999, 1547. (l) Paquette, L. A.; Lo, H. Y. J. Org. Chem. 2003, 68, 2282.
55. Syntheses of the fully functionalized Taxol CD ring unit: (a) Magee, T. V.; Bornmann, W. G.; Isaacs, R. C. A.; Danishefsky, S. J. J. Org. Chem. 1992, 57, 3274. (b) Nicolaou, K. C.; Liu, J. J.; Hwang, C.-K.; Dai, W.-M.; Guy, R. K. J. Chem. Soc., Chem. Commun. 1992, 1118. (c) Isaacs, R. C. A.; Di Grandi, M. J.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 3938. (d) Takahashi, T.; Hirose, Y.; Iwamoto, H.; Doi, T. J. Org. Chem. 1998, 63, 5742. (e) Nakada, M.; Kojima, E.-I.; Iwata, Y. Tetrahedron Lett. 1998, 39, 313. (f) Momose, T., Setoguchi, M.; Fujita, T.; Tamura, H.; Chida, N. Chem. Commun. 2000, 2237. (g) Nakai, K.; Miyamoto, S.; Sasuga, D.; Doi, T.; Takahashi, T. Tetrahedron Lett. 2001, 42, 7859. (h) Yoshimitsu, T.; Nakajima, H.; Nagaoka, H. Tetrahedron Lett. 2002, 43, 8587. (i) Shing, T. K. M.; Lee, C. M.; Lo, H. Y. Tetrahedron 2004, 60, 9179. Construction of the oxetane D ring in semisyntheses of taxanes which lacked functionality at C-7. (j) Potier's original procedure applied in numerous diversified methodologies: Ettovani, L.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1991, 47, 9823. (k) Zeng, Q.; Paquette, L. A. Synlett 1999, 1547. (l) Paquette, L. A.; Lo, H. Y. J. Org. Chem. 2003, 68, 2282.
56. Syntheses of the fully functionalized Taxol CD ring unit: (a) Magee, T. V.; Bornmann, W. G.; Isaacs, R. C. A.; Danishefsky, S. J. J. Org. Chem. 1992, 57, 3274. (b) Nicolaou, K. C.; Liu, J. J.; Hwang, C.-K.; Dai, W.-M.; Guy, R. K. J. Chem. Soc., Chem. Commun. 1992, 1118. (c) Isaacs, R. C. A.; Di Grandi, M. J.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 3938. (d) Takahashi, T.; Hirose, Y.; Iwamoto, H.; Doi, T. J. Org. Chem. 1998, 63, 5742. (e) Nakada, M.; Kojima, E.-I.; Iwata, Y. Tetrahedron Lett. 1998, 39, 313. (f) Momose, T., Setoguchi, M.; Fujita, T.; Tamura, H.; Chida, N. Chem. Commun. 2000, 2237. (g) Nakai, K.; Miyamoto, S.; Sasuga, D.; Doi, T.; Takahashi, T. Tetrahedron Lett. 2001, 42, 7859. (h) Yoshimitsu, T.; Nakajima, H.; Nagaoka, H. Tetrahedron Lett. 2002, 43, 8587. (i) Shing, T. K. M.; Lee, C. M.; Lo, H. Y. Tetrahedron 2004, 60, 9179. Construction of the oxetane D ring in semisyntheses of taxanes which lacked functionality at C-7. (j) Potier's original procedure applied in numerous diversified methodologies: Ettovani, L.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1991, 47, 9823. (k) Zeng, Q.; Paquette, L. A. Synlett 1999, 1547. (l) Paquette, L. A.; Lo, H. Y. J. Org. Chem. 2003, 68, 2282.
57. Syntheses of the fully functionalized Taxol CD ring unit: (a) Magee, T. V.; Bornmann, W. G.; Isaacs, R. C. A.; Danishefsky, S. J. J. Org. Chem. 1992, 57, 3274. (b) Nicolaou, K. C.; Liu, J. J.; Hwang, C.-K.; Dai, W.-M.; Guy, R. K. J. Chem. Soc., Chem. Commun. 1992, 1118. (c) Isaacs, R. C. A.; Di Grandi, M. J.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 3938. (d) Takahashi, T.; Hirose, Y.; Iwamoto, H.; Doi, T. J. Org. Chem. 1998, 63, 5742. (e) Nakada, M.; Kojima, E.-I.; Iwata, Y. Tetrahedron Lett. 1998, 39, 313. (f) Momose, T., Setoguchi, M.; Fujita, T.; Tamura, H.; Chida, N. Chem. Commun. 2000, 2237. (g) Nakai, K.; Miyamoto, S.; Sasuga, D.; Doi, T.; Takahashi, T. Tetrahedron Lett. 2001, 42, 7859. (h) Yoshimitsu, T.; Nakajima, H.; Nagaoka, H. Tetrahedron Lett. 2002, 43, 8587. (i) Shing, T. K. M.; Lee, C. M.; Lo, H. Y. Tetrahedron 2004, 60, 9179. Construction of the oxetane D ring in semisyntheses of taxanes which lacked functionality at C-7. (j) Potier's original procedure applied in numerous diversified methodologies: Ettovani, L.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1991, 47, 9823. (k) Zeng, Q.; Paquette, L. A. Synlett 1999, 1547. (l) Paquette, L. A.; Lo, H. Y. J. Org. Chem. 2003, 68, 2282.
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