Shin, Y and Fournier, JH and Brückner, A and Madiraju, C and Balachandran, R and Raccor, BS and Edler, MC and Hamel, E and Sikorski, RP and Vogt, A and Day, BW and Curran, DP
(2007)
Synthesis and biological evaluation of (-)-dictyostatin and stereoisomers.
Tetrahedron, 63 (35).
8537 - 8562.
ISSN 0040-4020
![[img]](http://d-scholarship-dev.library.pitt.edu/style/images/fileicons/text_plain.png) |
Plain Text (licence)
Available under License : See the attached license file.
Download (1kB)
|
Abstract
Total syntheses of (-)-dictyostatin, 6,16-bis-epi-dictyostatin, 6,14,19-tris-epi-dictyostatin, and a number of other isomers and analogs are reported. Three main fragments-top, middle, and bottom-were first assembled and then joined by olefination or anionic addition reactions. After appending the two dienes at either end of the molecule, macrolactonization and deprotection completed the syntheses. The work proves both the relative and absolute configurations of (-)-dictyostatin. The compounds were evaluated by cell-based measurements of increased microtubule mass and antiproliferative activity, and in vitro tubulin polymerization assays as well as competitive assays with paclitaxel for its binding site on microtubules. These assays showed dictyostatin to be the most potent of the agents and further showed that the structural alterations caused from 20- to >1000-fold decreases in activity. © 2007 Elsevier Ltd. All rights reserved.
Share
Citation/Export: |
|
Social Networking: |
|
Details
Item Type: |
Article
|
Status: |
Published |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID ![](/images/orcid_id_24x24.png) |
---|
Shin, Y | | | | Fournier, JH | | | | Brückner, A | | | | Madiraju, C | | | | Balachandran, R | | | | Raccor, BS | | | | Edler, MC | | | | Hamel, E | | | | Sikorski, RP | | | | Vogt, A | | | | Day, BW | | | | Curran, DP | curran@pitt.edu | CURRAN | |
|
Date: |
27 August 2007 |
Date Type: |
Publication |
Journal or Publication Title: |
Tetrahedron |
Volume: |
63 |
Number: |
35 |
Page Range: |
8537 - 8562 |
DOI or Unique Handle: |
10.1016/j.tet.2007.05.033 |
Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
Refereed: |
Yes |
ISSN: |
0040-4020 |
PubMed Central ID: |
PMC2000856 |
PubMed ID: |
18728696 |
Date Deposited: |
02 May 2013 20:25 |
Last Modified: |
02 Feb 2019 15:58 |
URI: |
http://d-scholarship-dev.library.pitt.edu/id/eprint/18564 |
Metrics
Monthly Views for the past 3 years
Plum Analytics
Altmetric.com
Actions (login required)
![View Item View Item](/style/images/action_view.png) |
View Item |