A stereocontrolled synthesis of delta-trans-tocotrienoloic acid.
[reaction: see text] A concise stereoselective total synthesis of a naturally occurring polymerase beta inhibitor, delta-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 beta inhibition.
Maloney
David J
DJ
Department of Chemistry, University of Virginia, Charlottesville, Virginia 22901, USA.
Hecht
Sidney M
SM
D000478:Alkylation; D003500:Cyclization; D003890:Desiccation; D006859:Hydrogen / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014810:Vitamin E / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D007454:Iodides; C094653:tocotrienoloic acid; D014810:Vitamin E; D006859:Hydrogen