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

doi:10.1021/ol047686a

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

Molecular Pharmacology

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

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 language	English (US)
Pages (from-to)	311-314
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	2
DOIs	https://doi.org/10.1021/ol047686a
State	Published - Jan 20 2005

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol047686a

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

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.",

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

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T1 - Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide

AU - Smith, Amos B.

AU - Freeze, B. Scott

AU - LaMarche, Matthew J.

AU - Hirose, Tomoyasu

AU - Brouard, Ignacio

AU - Rucker, Paul V.

AU - Xian, Ming

AU - Sundermann, Kurt F.

AU - Shaw, Simon J.

AU - Burlingame, Mark A.

AU - Horwitz, Susan Band

AU - Myles, David C.

PY - 2005/1/20

Y1 - 2005/1/20

N2 - (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.

AB - (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.

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JF - Organic Letters

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ER -

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

Abstract

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