| Nazarov cyclization initiated by peracid oxidation: the total synthesis of (+/-)-rocaglamide. | |
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MedLine Citation:
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PMID: 19445456 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The total syntheses of aglafolin, rocagloic acid, and rocaglamide using Nazarov cyclization are described. Generation of the necessary oxyallyl cation intermediate was accomplished via peracid oxidation of an allenol ether to generate an unusual oxycarbenium ion species that undergoes cyclization. The synthesis is efficient, highly diastereoselective, and strategically distinct from previous syntheses of rocaglamide. |
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Authors:
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John A Malona; Kevin Cariou; Alison J Frontier |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, U.S. Gov't, Non-P.H.S. |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 131 ISSN: 1520-5126 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2009 Jun |
Date Detail:
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Created Date: 2009-06-03 Completed Date: 2009-07-22 Revised Date: 2013-04-12 |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: United States |
Other Details:
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Languages: eng Pagination: 7560-1 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of Rochester, Rochester, New York 14627, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Benzofurans
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chemical synthesis* Cyclization Epoxy Compounds / chemistry Oxidation-Reduction Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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R01 GM079364/GM/NIGMS NIH HHS; R01 GM079364-01/GM/NIGMS NIH HHS; R01 GM079364-02/GM/NIGMS NIH HHS; R01 GM079364-03/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Benzofurans; 0/Epoxy Compounds; 84573-16-0/rocaglamide |
| Comments/Corrections | |
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