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Literature DB >> 19847350

The development of endo-selective epoxide-opening cascades in water.

Christopher J Morten¹, Jeffery A Byers, Aaron R Van Dyke, Ivan Vilotijevic, Timothy F Jamison.

Abstract

This tutorial review traces the development of endo-regioselective epoxide-opening reactions in water. Templated, water-promoted epoxide-opening cyclization reactions can offer rapid access to subunits of the ladder polyethers, a fascinating and complex family of natural products. This review may be of interest to those curious about the ladder polyethers and their hypothesized biogenesis, about organic reactions in water, and about the development and application of cascade reactions in organic synthesis.

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Year: 2009 PMID： 19847350 PMCID： PMC2805183 DOI： 10.1039/b816697h

Source DB: PubMed Journal: Chem Soc Rev ISSN： 0306-0012 Impact factor: 54.564

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6. Hot water-promoted ring-opening of epoxides and aziridines by water and other nucleopliles.

Authors: Zhi Wang; Yong-Tao Cui; Zhao-Bing Xu; Jin Qu
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Review 7. Epoxide-opening cascades in the synthesis of polycyclic polyether natural products.

Authors: Ivan Vilotijevic; Timothy F Jamison
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

8. SiMe3-based homologation-epoxidation-cyclization strategy for ladder THP synthesis.

Authors: Timothy P Heffron; Timothy F Jamison
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9. Polyketide synthase genes from marine dinoflagellates.

Authors: R V Snyder; P D L Gibbs; A Palacios; L Abiy; R Dickey; J V Lopez; K S Rein
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10. An experimental and computational approach to defining structure/reactivity relationships for intramolecular addition reactions to bicyclic epoxonium ions.

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Authors: Mina Razzak; Jef K De Brabander
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2. Entropic factors provide unusual reactivity and selectivity in epoxide-opening reactions promoted by water.

Authors: Jeffery A Byers; Timothy F Jamison
Journal: Proc Natl Acad Sci U S A Date: 2013-09-17 Impact factor: 11.205

3. Hydroxyl-substituted ladder polyethers via selective tandem epoxidation/cyclization sequence.

Authors: Lara C Czabaniuk; Timothy F Jamison
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Review 5. Ring opening of epoxides with C-nucleophiles.

Authors: Sadia Faiz; Ameer Fawad Zahoor
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6. Evidence that epoxide-opening cascades promoted by water are stepwise and become faster and more selective after the first cyclization.

Authors: Christopher J Morten; Jeffery A Byers; Timothy F Jamison
Journal: J Am Chem Soc Date: 2011-01-14 Impact factor: 15.419

10. Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades.

Authors: Brian S Underwood; Jessica Tanuwidjaja; Sze-Sze Ng; Timothy F Jamison
Journal: Tetrahedron Date: 2013-06-24 Impact factor: 2.457