Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide

Amos B. Smith, B. Scott Freeze, Matthew J. LaMarche, Tomoyasu Hirose, Ignacio Brouard, Paul V. Rucker, Ming Xian, Kurt F. Sundermann, Simon J. Shaw, Mark A. Burlingame, Susan Band Horwitz, David C. Myles

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Abstract

(Chemical Equation Presented) The design, syntheses, and biological evaluation of 22 totally synthetic analogues of the potent microtubule- stabilizing agent (+)-discodermolide (1) have been achieved. Structure-activity relationships of the C(19) carbamate were defined, exploiting two synthetically simplified scaffolds, as well as the parent (+)-discodermolide framework.

Original languageEnglish (US)
Pages (from-to)311-314
Number of pages4
JournalOrganic Letters
Volume7
Issue number2
DOIs
Publication statusPublished - Jan 20 2005

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Smith, A. B., Freeze, B. S., LaMarche, M. J., Hirose, T., Brouard, I., Rucker, P. V., ... Myles, D. C. (2005). Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide. Organic Letters, 7(2), 311-314. https://doi.org/10.1021/ol047686a