Document Detail


Exercising regiocontrol in palladium-catalyzed asymmetric prenylations and geranylation: unifying strategy toward flustramines A and B.
MedLine Citation:
PMID:  21520958     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Barry M Trost; Sushant Malhotra; Walter H Chan
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Publication Detail:
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:
Title:  Journal of the American Chemical Society     Volume:  133     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2011 May 
Date Detail:
Created Date:  2011-05-11     Completed Date:  2011-08-30     Revised Date:  2014-09-16    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  7328-31     Citation Subset:  IM    
Copyright Information:
© 2011 American Chemical Society
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MeSH Terms
Descriptor/Qualifier:
Catalysis
Geranyltranstransferase / chemistry
Indole Alkaloids / chemistry*
Molecular Structure
Palladium / chemistry*
Prenylation
Stereoisomerism
Grant Support
ID/Acronym/Agency:
GM033049/GM/NIGMS NIH HHS; R01 GM033049/GM/NIGMS NIH HHS; R01 GM033049-36/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Indole Alkaloids; 5TWQ1V240M/Palladium; 71239-64-0/flustramine A; 71239-65-1/flustramine B; EC 2.5.1.10/Geranyltranstransferase
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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