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Selective synthesis of (2Z,4E)-dienyl esters by ene-diene cross metathesis

Moura-Letts, G and Curran, DP (2007) Selective synthesis of (2Z,4E)-dienyl esters by ene-diene cross metathesis. Organic Letters, 9 (1). 5 - 8. ISSN 1523-7060

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(Chemical Equation Presented) Cross metathesis of terminal alkenes with methyl (2Z4E)-hexadienoate and related dienyl esters provides substituted (2Z,4E)-dienyl esters in good yields. Small-scale reactions are effectively promoted by the standard second-generation Grubbs-Hoveyda catalyst (GH-II), while a new fluorous GH-II catalyst is used for separation and recovery in gram-scale reactions. The transformation is featured in a rapid synthesis of the bottom fragments of the potent anticancer agents (-)-dictyostatin and 6-epi-dictyostatin. © 2007 American Chemical Society.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Moura-Letts, G
Curran, DPcurran@pitt.eduCURRAN
Date: 4 January 2007
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 9
Number: 1
Page Range: 5 - 8
DOI or Unique Handle: 10.1021/ol062017d
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Catalysis; Esters--chemical synthesis; Esters--chemistry; Macrolides--chemistry; Molecular Structure; Solvents
Other ID: NLM NIHMS63824, NLM PMC2535931
PubMed Central ID: PMC2535931
PubMed ID: 17192071
Date Deposited: 30 Apr 2013 21:01
Last Modified: 02 Feb 2019 15:58


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