Stereoselective synthesis of the C15-C24 fragment of discodermolide by desymmetrization of a meso dialdehyde

Synlett

Volumn , Issue 11, 2004, Pages 2034-2036

  BouzBouz, Samir ^a   Cossy, Janine ^a  

^a CNRS   (France)

Author keywords

Crotyltitanation; Desymmetrization; Discodermolide; meso dialdehyde

Indexed keywords

ALDEHYDE DERIVATIVE; DISCODERMOLIDE; TITANIUM DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; DESYMMETRIZATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 4544225535     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-830882     Document Type: Article

References (29)

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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. (f) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P. Angew. Chem. Int. Ed. 2000, 39, 377. (g) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001, 123, 9535. (h) Halstead, D. P. Ph.D. Thesis; Harvard University: Cambridge, MA, 1998.
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. (f) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P. Angew. Chem. Int. Ed. 2000, 39, 377. (g) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001, 123, 9535. (h) Halstead, D. P. Ph.D. Thesis; Harvard University: Cambridge, MA, 1998.
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. (f) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P. Angew. Chem. Int. Ed. 2000, 39, 377. (g) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001, 123, 9535. (h) Halstead, D. P. Ph.D. Thesis; Harvard University: Cambridge, MA, 1998.
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. (f) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P. Angew. Chem. Int. Ed. 2000, 39, 377. (g) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001, 123, 9535. (h) Halstead, D. P. Ph.D. Thesis; Harvard University: Cambridge, MA, 1998.
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. (f) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P. Angew. Chem. Int. Ed. 2000, 39, 377. (g) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001, 123, 9535. (h) Halstead, D. P. Ph.D. Thesis; Harvard University: Cambridge, MA, 1998.
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. (f) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P. Angew. Chem. Int. Ed. 2000, 39, 377. (g) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001, 123, 9535. (h) Halstead, D. P. Ph.D. Thesis; Harvard University: Cambridge, MA, 1998.
19. 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. (f) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P. Angew. Chem. Int. Ed. 2000, 39, 377. (g) Paterson, I.; Florence, G. J.; Gerlach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001, 123, 9535. (h) Halstead, D. P. Ph.D. Thesis; Harvard University: Cambridge, MA, 1998.
20. Formal synthesis: Francavilla, C.; Chen, W.; Kinder, F. R. Jr. Org. Lett. 2003, 5, 1233.
21. For synthetic approaches to discodermolide, see: (a) Arefolov, A.; Panek, J. S. Org. Lett. 2002, 4, 2397; and references therein, (b) Bazan-Tejeda, B.; Georgy, M.; Campagne, J. M. Synlett 2004, 720.
22. For synthetic approaches to discodermolide, see: (a) Arefolov, A.; Panek, J. S. Org. Lett. 2002, 4, 2397; and references therein, (b) Bazan-Tejeda, B.; Georgy, M.; Campagne, J. M. Synlett 2004, 720.
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28. -1. MS (EI, 70 eV): m/z (%) = 386 [M, absent], 329 (19) [M - t-Bu], 283 (11), 267 (100), 249 (37), 213 (27), 183 (38), 145 (72), 122 (71), 89 (55), 75 (48).
29. -1.