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Volumn 44, Issue 49, 2003, Pages 8877-8882

Synthesis of novel discodermolide analogues with modified hydrogen-bonding donor/acceptor sites

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DISCODERMOLIDE; HYDROGEN; TUBULIN;

EID: 0242266535     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.172     Document Type: Article
Times cited : (12)

References (35)
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    • In each case, we found several discrete families of low energy conformations, as anticipated from the results of Snyder and co-workers. For conformational studies on discodermolide, see: (a) Monteagudo, E.; Cicero, D. O.; Cornett, B.; Myles D. C.; Snyder, J. P. J. Am. Chem. Soc. 2001, 123, 6929; (b) Smith, A. B., III; La Marche, M. J.; Falcone-Hindley, M. Org. Lett. 2001, 3, 695.
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    • In each case, we found several discrete families of low energy conformations, as anticipated from the results of Snyder and co-workers. For conformational studies on discodermolide, see: (a) Monteagudo, E.; Cicero, D. O.; Cornett, B.; Myles D. C.; Snyder, J. P. J. Am. Chem. Soc. 2001, 123, 6929; (b) Smith, A. B., III; La Marche, M. J.; Falcone-Hindley, M. Org. Lett. 2001, 3, 695.
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    • note
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  • 34
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    • On acid treatment of 19, rapid deprotection of the two TBS groups and the TES group was accomplished in 80% yield in 1 h. In contrast, the TBS ether at C3 on the δ-lactone of discodermolide requires prolonged treatment with acid (2-3 days) for complete removal and this was found to be incompatible with the oxetane group
    • On acid treatment of 19, rapid deprotection of the two TBS groups and the TES group was accomplished in 80% yield in 1 h. In contrast, the TBS ether at C3 on the δ-lactone of discodermolide requires prolonged treatment with acid (2-3 days) for complete removal and this was found to be incompatible with the oxetane group.
  • 35
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    • + 615.3509, found 615.3516.


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