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

Research output: Contribution to journalArticle

33 Citations (Scopus)

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
StatePublished - Jan 20 2005

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Excipients
dienes
Lactones
Structure-Activity Relationship
simplification
Microtubules
analogs
evaluation
synthesis
14-normethyldiscodermolide

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Smith, A. B., Freeze, B. S., LaMarche, M. J., Hirose, T., Brouard, I., Xian, M., ... Myles, D. C. (2005). Design, synthesis, and evaluation of analogues of (+)-14- normethyldiscodermolide. Organic Letters, 7(2), 315-318.

Design, synthesis, and evaluation of analogues of (+)-14- normethyldiscodermolide. / Smith, Amos B.; Freeze, B. Scott; LaMarche, Matthew J.; Hirose, Tomoyasu; Brouard, Ignacio; Xian, Ming; Sundermann, Kurt F.; Shaw, Simon J.; Burlingame, Mark A.; Band Horwitz, Susan; Myles, David C.

In: Organic Letters, Vol. 7, No. 2, 20.01.2005, p. 315-318.

Research output: Contribution to journalArticle

Smith, AB, Freeze, BS, LaMarche, MJ, Hirose, T, Brouard, I, Xian, M, Sundermann, KF, Shaw, SJ, Burlingame, MA, Band Horwitz, S & Myles, DC 2005, 'Design, synthesis, and evaluation of analogues of (+)-14- normethyldiscodermolide', Organic Letters, vol. 7, no. 2, pp. 315-318.
Smith AB, Freeze BS, LaMarche MJ, Hirose T, Brouard I, Xian M et al. Design, synthesis, and evaluation of analogues of (+)-14- normethyldiscodermolide. Organic Letters. 2005 Jan 20;7(2):315-318.
Smith, Amos B. ; Freeze, B. Scott ; LaMarche, Matthew J. ; Hirose, Tomoyasu ; Brouard, Ignacio ; Xian, Ming ; Sundermann, Kurt F. ; Shaw, Simon J. ; Burlingame, Mark A. ; Band Horwitz, Susan ; Myles, David C. / Design, synthesis, and evaluation of analogues of (+)-14- normethyldiscodermolide. In: Organic Letters. 2005 ; Vol. 7, No. 2. pp. 315-318.
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