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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Abstract

(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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Details

Item Type:	Article
Status:	Published
Creators/Authors:	Creators Email Pitt Username ORCID Moura-Letts, G Curran, DP curran@pitt.edu CURRAN
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
URI:	http://d-scholarship.pitt.edu/id/eprint/18573

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