Taxol semisynthesis: A highly enantio- and diastereoselective synthesis of the side chain and a new method for ester formation at C-13 using thioesters

Journal of Organic Chemistry

Volumn 62, Issue 14, 1997, Pages 4746-4755

  Gennari, Cesare ^a   Carcano, Michela ^a   Donghi, Monica ^a   Mongelli, Nicola ^b   Vanotti, Ermes ^b   Vulpetti, Anna ^a,b  

^a UNIVERSITY OF MILAN   (Italy)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DOCETAXEL; PACLITAXEL;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CHEMOTHERAPY; DRUG SYNTHESIS; OVARY METASTASIS; STEREOCHEMISTRY;

EID: 0030836632     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9703212     Document Type: Article

References (103)

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51. For applications after 1993, see: (a) Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Soresen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633. (b) Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597-1598. (c) Ojima, I.; Park, Y. H.; Sun, C.-M.; Fenoglio, I.; Appendino, G.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1994, 37, 1408-1410. J. Org. Chem. 1994, 59, 515-517. (d) Holton, R. A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668. (e) Nicolaou, K. C. et al. Nature 1994, 367, 630-634. (f) Kant, J.; O'Keeffe, W. S.; Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F.; Long, B. H.; Vyas, D. Tetrahedron Lett. 1994, 35, 5543-5546. (g) Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F. J. Org. Chem. 1994, 59, 6156-6158. (h) Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. J. Med. Chem. 1994, 37, 3337-3343. (i) Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409-2420. (j) Young, W. B.; Masters, J. J.; Danishefsky, S. J. Am. Chem. Soc. 1995, 117, 5228-5234. (k) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. 1995, 107, 1886-1888; Angew. Chem., Int. Ed. Engl. 1995, 34, 1723-1726. (l) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vander Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676. (m) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. (n) Park, H.; Hepperle, M.; Boge, T. C.; Himes, R. H.; Georg, G. I. J. Med. Chem. 1996, 39, 2705-2709.
52. For applications after 1993, see: (a) Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Soresen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633. (b) Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597-1598. (c) Ojima, I.; Park, Y. H.; Sun, C.-M.; Fenoglio, I.; Appendino, G.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1994, 37, 1408-1410. J. Org. Chem. 1994, 59, 515-517. (d) Holton, R. A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668. (e) Nicolaou, K. C. et al. Nature 1994, 367, 630-634. (f) Kant, J.; O'Keeffe, W. S.; Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F.; Long, B. H.; Vyas, D. Tetrahedron Lett. 1994, 35, 5543-5546. (g) Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F. J. Org. Chem. 1994, 59, 6156-6158. (h) Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. J. Med. Chem. 1994, 37, 3337-3343. (i) Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409-2420. (j) Young, W. B.; Masters, J. J.; Danishefsky, S. J. Am. Chem. Soc. 1995, 117, 5228-5234. (k) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. 1995, 107, 1886-1888; Angew. Chem., Int. Ed. Engl. 1995, 34, 1723-1726. (l) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vander Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676. (m) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. (n) Park, H.; Hepperle, M.; Boge, T. C.; Himes, R. H.; Georg, G. I. J. Med. Chem. 1996, 39, 2705-2709.
53. For applications after 1993, see: (a) Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Soresen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633. (b) Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597-1598. (c) Ojima, I.; Park, Y. H.; Sun, C.-M.; Fenoglio, I.; Appendino, G.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1994, 37, 1408-1410. J. Org. Chem. 1994, 59, 515-517. (d) Holton, R. A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668. (e) Nicolaou, K. C. et al. Nature 1994, 367, 630-634. (f) Kant, J.; O'Keeffe, W. S.; Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F.; Long, B. H.; Vyas, D. Tetrahedron Lett. 1994, 35, 5543-5546. (g) Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F. J. Org. Chem. 1994, 59, 6156-6158. (h) Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. J. Med. Chem. 1994, 37, 3337-3343. (i) Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409-2420. (j) Young, W. B.; Masters, J. J.; Danishefsky, S. J. Am. Chem. Soc. 1995, 117, 5228-5234. (k) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. 1995, 107, 1886-1888; Angew. Chem., Int. Ed. Engl. 1995, 34, 1723-1726. (l) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vander Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676. (m) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. (n) Park, H.; Hepperle, M.; Boge, T. C.; Himes, R. H.; Georg, G. I. J. Med. Chem. 1996, 39, 2705-2709.
54. For applications after 1993, see: (a) Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Soresen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633. (b) Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597-1598. (c) Ojima, I.; Park, Y. H.; Sun, C.-M.; Fenoglio, I.; Appendino, G.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1994, 37, 1408-1410. J. Org. Chem. 1994, 59, 515-517. (d) Holton, R. A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668. (e) Nicolaou, K. C. et al. Nature 1994, 367, 630-634. (f) Kant, J.; O'Keeffe, W. S.; Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F.; Long, B. H.; Vyas, D. Tetrahedron Lett. 1994, 35, 5543-5546. (g) Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F. J. Org. Chem. 1994, 59, 6156-6158. (h) Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. J. Med. Chem. 1994, 37, 3337-3343. (i) Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409-2420. (j) Young, W. B.; Masters, J. J.; Danishefsky, S. J. Am. Chem. Soc. 1995, 117, 5228-5234. (k) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. 1995, 107, 1886-1888; Angew. Chem., Int. Ed. Engl. 1995, 34, 1723-1726. (l) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vander Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676. (m) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. (n) Park, H.; Hepperle, M.; Boge, T. C.; Himes, R. H.; Georg, G. I. J. Med. Chem. 1996, 39, 2705-2709.
55. For applications after 1993, see: (a) Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Soresen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633. (b) Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597-1598. (c) Ojima, I.; Park, Y. H.; Sun, C.-M.; Fenoglio, I.; Appendino, G.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1994, 37, 1408-1410. J. Org. Chem. 1994, 59, 515-517. (d) Holton, R. A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668. (e) Nicolaou, K. C. et al. Nature 1994, 367, 630-634. (f) Kant, J.; O'Keeffe, W. S.; Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F.; Long, B. H.; Vyas, D. Tetrahedron Lett. 1994, 35, 5543-5546. (g) Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F. J. Org. Chem. 1994, 59, 6156-6158. (h) Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. J. Med. Chem. 1994, 37, 3337-3343. (i) Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409-2420. (j) Young, W. B.; Masters, J. J.; Danishefsky, S. J. Am. Chem. Soc. 1995, 117, 5228-5234. (k) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. 1995, 107, 1886-1888; Angew. Chem., Int. Ed. Engl. 1995, 34, 1723-1726. (l) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vander Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676. (m) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. (n) Park, H.; Hepperle, M.; Boge, T. C.; Himes, R. H.; Georg, G. I. J. Med. Chem. 1996, 39, 2705-2709.
56. For applications after 1993, see: (a) Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Soresen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633. (b) Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597-1598. (c) Ojima, I.; Park, Y. H.; Sun, C.-M.; Fenoglio, I.; Appendino, G.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1994, 37, 1408-1410. J. Org. Chem. 1994, 59, 515-517. (d) Holton, R. A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668. (e) Nicolaou, K. C. et al. Nature 1994, 367, 630-634. (f) Kant, J.; O'Keeffe, W. S.; Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F.; Long, B. H.; Vyas, D. Tetrahedron Lett. 1994, 35, 5543-5546. (g) Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F. J. Org. Chem. 1994, 59, 6156-6158. (h) Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. J. Med. Chem. 1994, 37, 3337-3343. (i) Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409-2420. (j) Young, W. B.; Masters, J. J.; Danishefsky, S. J. Am. Chem. Soc. 1995, 117, 5228-5234. (k) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. 1995, 107, 1886-1888; Angew. Chem., Int. Ed. Engl. 1995, 34, 1723-1726. (l) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vander Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676. (m) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. (n) Park, H.; Hepperle, M.; Boge, T. C.; Himes, R. H.; Georg, G. I. J. Med. Chem. 1996, 39, 2705-2709.
57. For applications after 1993, see: (a) Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Soresen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633. (b) Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597-1598. (c) Ojima, I.; Park, Y. H.; Sun, C.-M.; Fenoglio, I.; Appendino, G.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1994, 37, 1408-1410. J. Org. Chem. 1994, 59, 515-517. (d) Holton, R. A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668. (e) Nicolaou, K. C. et al. Nature 1994, 367, 630-634. (f) Kant, J.; O'Keeffe, W. S.; Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F.; Long, B. H.; Vyas, D. Tetrahedron Lett. 1994, 35, 5543-5546. (g) Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F. J. Org. Chem. 1994, 59, 6156-6158. (h) Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. J. Med. Chem. 1994, 37, 3337-3343. (i) Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409-2420. (j) Young, W. B.; Masters, J. J.; Danishefsky, S. J. Am. Chem. Soc. 1995, 117, 5228-5234. (k) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. 1995, 107, 1886-1888; Angew. Chem., Int. Ed. Engl. 1995, 34, 1723-1726. (l) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vander Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676. (m) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. (n) Park, H.; Hepperle, M.; Boge, T. C.; Himes, R. H.; Georg, G. I. J. Med. Chem. 1996, 39, 2705-2709.
58. For applications after 1993, see: (a) Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Soresen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633. (b) Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597-1598. (c) Ojima, I.; Park, Y. H.; Sun, C.-M.; Fenoglio, I.; Appendino, G.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1994, 37, 1408-1410. J. Org. Chem. 1994, 59, 515-517. (d) Holton, R. A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668. (e) Nicolaou, K. C. et al. Nature 1994, 367, 630-634. (f) Kant, J.; O'Keeffe, W. S.; Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F.; Long, B. H.; Vyas, D. Tetrahedron Lett. 1994, 35, 5543-5546. (g) Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F. J. Org. Chem. 1994, 59, 6156-6158. (h) Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. J. Med. Chem. 1994, 37, 3337-3343. (i) Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409-2420. (j) Young, W. B.; Masters, J. J.; Danishefsky, S. J. Am. Chem. Soc. 1995, 117, 5228-5234. (k) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. 1995, 107, 1886-1888; Angew. Chem., Int. Ed. Engl. 1995, 34, 1723-1726. (l) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vander Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676. (m) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. (n) Park, H.; Hepperle, M.; Boge, T. C.; Himes, R. H.; Georg, G. I. J. Med. Chem. 1996, 39, 2705-2709.
59. For applications after 1993, see: (a) Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Soresen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633. (b) Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597-1598. (c) Ojima, I.; Park, Y. H.; Sun, C.-M.; Fenoglio, I.; Appendino, G.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1994, 37, 1408-1410. J. Org. Chem. 1994, 59, 515-517. (d) Holton, R. A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668. (e) Nicolaou, K. C. et al. Nature 1994, 367, 630-634. (f) Kant, J.; O'Keeffe, W. S.; Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F.; Long, B. H.; Vyas, D. Tetrahedron Lett. 1994, 35, 5543-5546. (g) Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F. J. Org. Chem. 1994, 59, 6156-6158. (h) Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. J. Med. Chem. 1994, 37, 3337-3343. (i) Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409-2420. (j) Young, W. B.; Masters, J. J.; Danishefsky, S. J. Am. Chem. Soc. 1995, 117, 5228-5234. (k) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. 1995, 107, 1886-1888; Angew. Chem., Int. Ed. Engl. 1995, 34, 1723-1726. (l) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vander Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676. (m) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. (n) Park, H.; Hepperle, M.; Boge, T. C.; Himes, R. H.; Georg, G. I. J. Med. Chem. 1996, 39, 2705-2709.
60. For applications after 1993, see: (a) Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Soresen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633. (b) Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597-1598. (c) Ojima, I.; Park, Y. H.; Sun, C.-M.; Fenoglio, I.; Appendino, G.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1994, 37, 1408-1410. J. Org. Chem. 1994, 59, 515-517. (d) Holton, R. A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668. (e) Nicolaou, K. C. et al. Nature 1994, 367, 630-634. (f) Kant, J.; O'Keeffe, W. S.; Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F.; Long, B. H.; Vyas, D. Tetrahedron Lett. 1994, 35, 5543-5546. (g) Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F. J. Org. Chem. 1994, 59, 6156-6158. (h) Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. J. Med. Chem. 1994, 37, 3337-3343. (i) Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409-2420. (j) Young, W. B.; Masters, J. J.; Danishefsky, S. J. Am. Chem. Soc. 1995, 117, 5228-5234. (k) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. 1995, 107, 1886-1888; Angew. Chem., Int. Ed. Engl. 1995, 34, 1723-1726. (l) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vander Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676. (m) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. (n) Park, H.; Hepperle, M.; Boge, T. C.; Himes, R. H.; Georg, G. I. J. Med. Chem. 1996, 39, 2705-2709.
61. For applications after 1993, see: (a) Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Soresen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633. (b) Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597-1598. (c) Ojima, I.; Park, Y. H.; Sun, C.-M.; Fenoglio, I.; Appendino, G.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1994, 37, 1408-1410. J. Org. Chem. 1994, 59, 515-517. (d) Holton, R. A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668. (e) Nicolaou, K. C. et al. Nature 1994, 367, 630-634. (f) Kant, J.; O'Keeffe, W. S.; Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F.; Long, B. H.; Vyas, D. Tetrahedron Lett. 1994, 35, 5543-5546. (g) Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F. J. Org. Chem. 1994, 59, 6156-6158. (h) Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. J. Med. Chem. 1994, 37, 3337-3343. (i) Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409-2420. (j) Young, W. B.; Masters, J. J.; Danishefsky, S. J. Am. Chem. Soc. 1995, 117, 5228-5234. (k) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. 1995, 107, 1886-1888; Angew. Chem., Int. Ed. Engl. 1995, 34, 1723-1726. (l) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vander Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676. (m) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. (n) Park, H.; Hepperle, M.; Boge, T. C.; Himes, R. H.; Georg, G. I. J. Med. Chem. 1996, 39, 2705-2709.
62. For applications after 1993, see: (a) Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Soresen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633. (b) Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597-1598. (c) Ojima, I.; Park, Y. H.; Sun, C.-M.; Fenoglio, I.; Appendino, G.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1994, 37, 1408-1410. J. Org. Chem. 1994, 59, 515-517. (d) Holton, R. A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668. (e) Nicolaou, K. C. et al. Nature 1994, 367, 630-634. (f) Kant, J.; O'Keeffe, W. S.; Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F.; Long, B. H.; Vyas, D. Tetrahedron Lett. 1994, 35, 5543-5546. (g) Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F. J. Org. Chem. 1994, 59, 6156-6158. (h) Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. J. Med. Chem. 1994, 37, 3337-3343. (i) Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409-2420. (j) Young, W. B.; Masters, J. J.; Danishefsky, S. J. Am. Chem. Soc. 1995, 117, 5228-5234. (k) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. 1995, 107, 1886-1888; Angew. Chem., Int. Ed. Engl. 1995, 34, 1723-1726. (l) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vander Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676. (m) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. (n) Park, H.; Hepperle, M.; Boge, T. C.; Himes, R. H.; Georg, G. I. J. Med. Chem. 1996, 39, 2705-2709.
63. For applications after 1993, see: (a) Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Soresen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633. (b) Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597-1598. (c) Ojima, I.; Park, Y. H.; Sun, C.-M.; Fenoglio, I.; Appendino, G.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1994, 37, 1408-1410. J. Org. Chem. 1994, 59, 515-517. (d) Holton, R. A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668. (e) Nicolaou, K. C. et al. Nature 1994, 367, 630-634. (f) Kant, J.; O'Keeffe, W. S.; Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F.; Long, B. H.; Vyas, D. Tetrahedron Lett. 1994, 35, 5543-5546. (g) Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F. J. Org. Chem. 1994, 59, 6156-6158. (h) Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. J. Med. Chem. 1994, 37, 3337-3343. (i) Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409-2420. (j) Young, W. B.; Masters, J. J.; Danishefsky, S. J. Am. Chem. Soc. 1995, 117, 5228-5234. (k) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. 1995, 107, 1886-1888; Angew. Chem., Int. Ed. Engl. 1995, 34, 1723-1726. (l) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vander Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676. (m) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. (n) Park, H.; Hepperle, M.; Boge, T. C.; Himes, R. H.; Georg, G. I. J. Med. Chem. 1996, 39, 2705-2709.
64. For applications after 1993, see: (a) Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Soresen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633. (b) Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597-1598. (c) Ojima, I.; Park, Y. H.; Sun, C.-M.; Fenoglio, I.; Appendino, G.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1994, 37, 1408-1410. J. Org. Chem. 1994, 59, 515-517. (d) Holton, R. A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668. (e) Nicolaou, K. C. et al. Nature 1994, 367, 630-634. (f) Kant, J.; O'Keeffe, W. S.; Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F.; Long, B. H.; Vyas, D. Tetrahedron Lett. 1994, 35, 5543-5546. (g) Chen, S.-H.; Farina, V.; Fairchild, C.; Johnston, K.; Kadow, J. F. J. Org. Chem. 1994, 59, 6156-6158. (h) Boge, T. C.; Himes, R. H.; Vander Velde, D. G.; Georg, G. I. J. Med. Chem. 1994, 37, 3337-3343. (i) Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409-2420. (j) Young, W. B.; Masters, J. J.; Danishefsky, S. J. Am. Chem. Soc. 1995, 117, 5228-5234. (k) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. 1995, 107, 1886-1888; Angew. Chem., Int. Ed. Engl. 1995, 34, 1723-1726. (l) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vander Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676. (m) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Langley, D. R.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. (n) Park, H.; Hepperle, M.; Boge, T. C.; Himes, R. H.; Georg, G. I. J. Med. Chem. 1996, 39, 2705-2709.
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