Document Detail


Phosphine/palladium-catalyzed syntheses of alkylidene phthalans, 3-deoxyisoochracinic acid, isoochracinic acid, and isoochracinol.
MedLine Citation:
PMID:  22721256     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
In this study we used sequential catalysis-PPh(3)--catalyzed nucleophilic addition followed by Pd(0)-catalyzed Heck cyclization--to construct complex functionalized alkylidene phthalans rapidly, in high yields, and with good stereoselectivities (E/Z ratios of up to 1:22). The scope of this Michael-Heck reaction includes substrates bearing various substituents around the alkylidene phthalan backbone. Applying this efficient sequential catalysis, we accomplished concise total syntheses of 3-deoxyisoochacinic acid, isoochracinic acid, and isoochracinol.
Authors:
Yi Chiao Fan; Ohyun Kwon
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2012-06-21
Journal Detail:
Title:  Organic letters     Volume:  14     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2012 Jul 
Date Detail:
Created Date:  2012-07-06     Completed Date:  2012-11-07     Revised Date:  2013-07-12    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3264-7     Citation Subset:  IM    
Affiliation:
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
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MeSH Terms
Descriptor/Qualifier:
Benzofurans / chemical synthesis*,  chemistry
Catalysis
Molecular Structure
Palladium / chemistry*
Phosphines / chemistry*
Phthalic Acids / chemical synthesis*,  chemistry
Stereoisomerism
Grant Support
ID/Acronym/Agency:
P41 GM081282/GM/NIGMS NIH HHS; P41GM081282/GM/NIGMS NIH HHS; R01 GM071779/GM/NIGMS NIH HHS; R01GM071779/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/3-deoxyisoochracinic acid; 0/Benzofurans; 0/Phosphines; 0/Phthalic Acids; 0/isoochracinic acid; 0/isoochracinol; 7440-05-3/Palladium; 7803-51-2/phosphine
Comments/Corrections

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