Stereoselective synthesis of the C1-C13 fragment of (+)-discodermolide using asymmetric allyltitanations

Organic Letters

Volumn 5, Issue 17, 2003, Pages 3029-3031

  BouzBouz, Samir ^a   Cossy, Janine ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE; DISCODERMOLIDE;

ARTICLE; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0141743762     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034958l     Document Type: Article

References (26)

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13. Total synthesis: (a) Smith, A. B., III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011. (b) Smith, A. B., III; Kaufman, M. D.; Beauchamp, T. J.; LaMarche, M. J.; Arimoto, H. Org. Lett. 1999, 1, 1823. (c) Haried, S. S.; Yang, G.; Strawn, M. A.; Myles D. C. J. Org. Chem. 1997, 62, 6098. (d) Marshall, J. A.; Lu, Z.-H.; Johns, B. A. J. Org. Chem. 1998, 63, 7885. (e) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P. Angew. Chem., Int. Ed. 2000, 39, 2, 377. (f) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001, 123, 9535. (g) Halstead, D. P. Ph.D. Thesis, Harvard University, Cambridge, MA, 1998. (h) Formal synthesis: Francavila, C.; Chen, W.; Kinder, F. R., Jr. Org. Lett. 2003, 5, 1233.
14. Total synthesis: (a) Smith, A. B., III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011. (b) Smith, A. B., III; Kaufman, M. D.; Beauchamp, T. J.; LaMarche, M. J.; Arimoto, H. Org. Lett. 1999, 1, 1823. (c) Haried, S. S.; Yang, G.; Strawn, M. A.; Myles D. C. J. Org. Chem. 1997, 62, 6098. (d) Marshall, J. A.; Lu, Z.-H.; Johns, B. A. J. Org. Chem. 1998, 63, 7885. (e) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P. Angew. Chem., Int. Ed. 2000, 39, 2, 377. (f) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001, 123, 9535. (g) Halstead, D. P. Ph.D. Thesis, Harvard University, Cambridge, MA, 1998. (h) Formal synthesis: Francavila, C.; Chen, W.; Kinder, F. R., Jr. Org. Lett. 2003, 5, 1233.
15. Total synthesis: (a) Smith, A. B., III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011. (b) Smith, A. B., III; Kaufman, M. D.; Beauchamp, T. J.; LaMarche, M. J.; Arimoto, H. Org. Lett. 1999, 1, 1823. (c) Haried, S. S.; Yang, G.; Strawn, M. A.; Myles D. C. J. Org. Chem. 1997, 62, 6098. (d) Marshall, J. A.; Lu, Z.-H.; Johns, B. A. J. Org. Chem. 1998, 63, 7885. (e) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P. Angew. Chem., Int. Ed. 2000, 39, 2, 377. (f) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001, 123, 9535. (g) Halstead, D. P. Ph.D. Thesis, Harvard University, Cambridge, MA, 1998. (h) Formal synthesis: Francavila, C.; Chen, W.; Kinder, F. R., Jr. Org. Lett. 2003, 5, 1233.
16. Total synthesis: (a) Smith, A. B., III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011. (b) Smith, A. B., III; Kaufman, M. D.; Beauchamp, T. J.; LaMarche, M. J.; Arimoto, H. Org. Lett. 1999, 1, 1823. (c) Haried, S. S.; Yang, G.; Strawn, M. A.; Myles D. C. J. Org. Chem. 1997, 62, 6098. (d) Marshall, J. A.; Lu, Z.-H.; Johns, B. A. J. Org. Chem. 1998, 63, 7885. (e) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P. Angew. Chem., Int. Ed. 2000, 39, 2, 377. (f) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001, 123, 9535. (g) Halstead, D. P. Ph.D. Thesis, Harvard University, Cambridge, MA, 1998. (h) Formal synthesis: Francavila, C.; Chen, W.; Kinder, F. R., Jr. Org. Lett. 2003, 5, 1233.
17. Total synthesis: (a) Smith, A. B., III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011. (b) Smith, A. B., III; Kaufman, M. D.; Beauchamp, T. J.; LaMarche, M. J.; Arimoto, H. Org. Lett. 1999, 1, 1823. (c) Haried, S. S.; Yang, G.; Strawn, M. A.; Myles D. C. J. Org. Chem. 1997, 62, 6098. (d) Marshall, J. A.; Lu, Z.-H.; Johns, B. A. J. Org. Chem. 1998, 63, 7885. (e) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P. Angew. Chem., Int. Ed. 2000, 39, 2, 377. (f) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001, 123, 9535. (g) Halstead, D. P. Ph.D. Thesis, Harvard University, Cambridge, MA, 1998. (h) Formal synthesis: Francavila, C.; Chen, W.; Kinder, F. R., Jr. Org. Lett. 2003, 5, 1233.
18. Total synthesis: (a) Smith, A. B., III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011. (b) Smith, A. B., III; Kaufman, M. D.; Beauchamp, T. J.; LaMarche, M. J.; Arimoto, H. Org. Lett. 1999, 1, 1823. (c) Haried, S. S.; Yang, G.; Strawn, M. A.; Myles D. C. J. Org. Chem. 1997, 62, 6098. (d) Marshall, J. A.; Lu, Z.-H.; Johns, B. A. J. Org. Chem. 1998, 63, 7885. (e) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P. Angew. Chem., Int. Ed. 2000, 39, 2, 377. (f) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001, 123, 9535. (g) Halstead, D. P. Ph.D. Thesis, Harvard University, Cambridge, MA, 1998. (h) Formal synthesis: Francavila, C.; Chen, W.; Kinder, F. R., Jr. Org. Lett. 2003, 5, 1233.
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