A Stereocontrolled Synthesis of δ-trans-Tocotrienoloic Acid

A consise stereoselective total synthesis of a naturally occurring polymerase β inhibitor, δ-trans-tocotrienoloic acid (2), is described. The key step in the synthesis is an acid-catalyzed cyclodehydration reaction. Additionally, this report corrects a previously reported structural assignment, defi...

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Bibliographic Details
Published inOrganic letters Vol. 7; no. 19; pp. 4297 - 4300
Main Authors Maloney, David J, Hecht, Sidney M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.09.2005
Amer Chemical Soc
Subjects
Alkylation
Chemistry
Chemistry, Organic
Cyclization
Desiccation
Hydrogen - chemistry
Iodides - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
Vitamin E - analogs & derivatives
Vitamin E - chemical synthesis
Vitamin E - chemistry
VITAMIN-E
GARCINOIC ACID
CYCLIZATIONS
INHIBITORS
ALKYLATION
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Summary:A consise stereoselective total synthesis of a naturally occurring polymerase β inhibitor, δ-trans-tocotrienoloic acid (2), is described. The key step in the synthesis is an acid-catalyzed cyclodehydration reaction. Additionally, this report corrects a previously reported structural assignment, defines the absolute stereochemistry of 2, and defines key structural requirements for polymerase β inhibition.
Bibliography:Medline
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol051849t