| Exercising regiocontrol in palladium-catalyzed asymmetric prenylations and geranylation: unifying strategy toward flustramines A and B. | |
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MedLine Citation:
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PMID: 21520958 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Pd-catalyzed asymmetric prenylation of oxindoles to afford selectively either the prenyl or reverse-prenyl product has been demonstrated. Control of the regioselectivity in this transformation is governed by the choice of ligand, solvent, and halide additive. The resulting prenylated and reverse-prenylated products were transformed into ent-flustramides and ent-flustramines A and B. Additionally, control of the regio- and diastereoselectivity was obtained using π-geranylpalladium complexes. |
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Authors:
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Barry M Trost; Sushant Malhotra; Walter H Chan |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S. Date: 2011-04-26 |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 133 ISSN: 1520-5126 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2011 May |
Date Detail:
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Created Date: 2011-05-11 Completed Date: 2011-08-30 Revised Date: 2012-05-21 |
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: 7328-31 Citation Subset: IM |
Copyright Information:
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© 2011 American Chemical Society |
Affiliation:
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Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Catalysis Geranyltranstransferase / chemistry Indole Alkaloids / chemistry* Molecular Structure Palladium / chemistry* Prenylation Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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GM033049/GM/NIGMS NIH HHS; R01 GM033049-36/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Indole Alkaloids; 71239-64-0/flustramine A; 71239-65-1/flustramine B; 7440-05-3/Palladium; EC 2.5.1.10/Geranyltranstransferase |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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