Hopkins, CD and Schmitz, JC and Chu, E and Wipf, P
(2011)
Total synthesis of (-)-CP<inf>2</inf>-disorazole C<inf>1</inf>.
Organic Letters, 13 (15).
4088 - 4091.
ISSN 1523-7060
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Abstract
The total synthesis of a bis-cyclopropane analog of the antimitotic natural product (-)-disorazole C1 was accomplished in 23 steps and 1.1% overall yield. A vinyl cyclopropane cross-metathesis reaction generated a key (E)-alkene segment of the target molecule. IC50 determinations of (-)-CP2-disorazole C1 in human colon cancer cell lines indicated low nanomolar cytotoxic properties. Accordingly, this synthetic bioisostere represents the first biologically active disorazole analog not containing a conjugated diene or polyene substructure element. © 2011 American Chemical Society.
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Details
| Item Type: |
Article
|
| Status: |
Published |
| Creators/Authors: |
|
| Date: |
5 August 2011 |
| Date Type: |
Publication |
| Journal or Publication Title: |
Organic Letters |
| Volume: |
13 |
| Number: |
15 |
| Page Range: |
4088 - 4091 |
| DOI or Unique Handle: |
10.1021/ol2015994 |
| Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
| Refereed: |
Yes |
| ISSN: |
1523-7060 |
| MeSH Headings: |
Cell Line, Tumor; Cell Survival--drug effects; Ether, Ethyl--chemistry; Humans; Macrolides--chemical synthesis; Macrolides--pharmacology; Molecular Structure; Oxazoles--chemical synthesis; Oxazoles--pharmacology |
| Other ID: |
NLM NIHMS310695, NLM PMC3160746 |
| PubMed Central ID: |
PMC3160746 |
| PubMed ID: |
21739942 |
| Date Deposited: |
28 May 2013 15:25 |
| Last Modified: |
12 Jun 2021 22:55 |
| URI: |
http://d-scholarship-dev.library.pitt.edu/id/eprint/18739 |
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