Structural Revision and Total Synthesis of Caraphenol B and C

Chemical syntheses of two stereochemically unique resveratrol dimers, caraphenols B and C, have shown that their structures are misassigned. Thoughts on their potential chemical etiology led to an alternate structural proposal that has been confirmed through synthesis, one indicating that the substi...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 20; pp. 5524 - 5527
Main Authors Snyder, Scott A, Brill, Zachary G
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.10.2011
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Crystallography, X-Ray
Molecular Structure
Phenols - chemical synthesis
Phenols - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Stilbenes - chemical synthesis
Stilbenes - chemistry
RESVERATROL DIMER
HOPEAHAINOL
ROOTS
4-HYDROXYSTILBENES
STEM
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Summary:Chemical syntheses of two stereochemically unique resveratrol dimers, caraphenols B and C, have shown that their structures are misassigned. Thoughts on their potential chemical etiology led to an alternate structural proposal that has been confirmed through synthesis, one indicating that the substituents on their respective indane systems exist in a relative trans,trans orientation rather than the originally postulated all-cis arrangement.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol2022406