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Total synthesis of (-)-CP<inf>2</inf>-disorazole C<inf>1</inf>

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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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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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Hopkins, CD
Schmitz, JCjcs124@pitt.eduJCS124
Chu, Eedc16@pitt.eduEDC16
Wipf, Ppwipf@pitt.eduPWIPF
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: 22 Jun 2021 12:55


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