Design, synthesis, and evaluation of analogues of (+)-14- normethyldiscodermolide

Amos B. Smith, B. Scott Freeze, Matthew J. LaMarche, Tomoyasu Hirose, Ignacio Brouard, 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 nine totally synthetic analogues of the microtubule-stabilizing agent (+)-14-normethyldiscodermolide (2) are reported. Simplification at the C(21)-C(24) terminal diene and at the C(1)-C(5) lactone moieties reveals significant structure-activity relationships.

Original languageEnglish (US)
Pages (from-to)315-318
Number of pages4
JournalOrganic Letters
Volume7
Issue number2
DOIs
StatePublished - 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., Xian, M., Sundermann, K. F., Shaw, S. J., Burlingame, M. A., Horwitz, S. B., & Myles, D. C. (2005). Design, synthesis, and evaluation of analogues of (+)-14- normethyldiscodermolide. Organic Letters, 7(2), 315-318. https://doi.org/10.1021/ol0476873