Short Total Synthesis of 8,10-Di-O-methylbergenin

A short, high-yielding synthesis of the C-glucoside 8,10-di-O-methylbergenin is reported. Key elements of the synthesis are a stereoselective installation of a β-C-aryl linkage, a palladium(0)-catalyzed aryl carbonylation, and a regioselective lactonization reaction. This pathway should allow access...

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Bibliographic Details
Published inOrganic letters Vol. 4; no. 17; pp. 2965 - 2967
Main Authors Herzner, Holger, Palmacci, Emma R, Seeberger, Peter H
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 22.08.2002
Amer Chemical Soc
Subjects
Antiviral Agents - chemistry
Benzopyrans - chemical synthesis
Chemistry
Chemistry, Organic
Lactones - chemistry
Monosaccharides - chemical synthesis
Palladium - chemistry
Physical Sciences
Plants, Medicinal - chemistry
Science & Technology
ARYL C-GLYCOSIDES
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Summary:A short, high-yielding synthesis of the C-glucoside 8,10-di-O-methylbergenin is reported. Key elements of the synthesis are a stereoselective installation of a β-C-aryl linkage, a palladium(0)-catalyzed aryl carbonylation, and a regioselective lactonization reaction. This pathway should allow access to a host of bergenin analogues.
Bibliography:Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol026378e