Construction of 4-hydroxy-2-pyridinones. Total synthesis of (+)-sambutoxin.
Total synthesis of (+)-sambutoxin has been achieved, establishing the relative and absolute stereochemistry of the naturally occurring mycotoxin. Efforts feature methodology for enantiocontrolled construction of 1,3-anti-dimethyl arrays and a novel Saegusa oxidation to provide a pyridinone methide leading to formation of the central dihydropyran ring.
Williams
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Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, USA. williamd@indiana.edu
Turske
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RA
D005670:Fusarium / Q000737:chemistry; D009183:Mycotoxins / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009183:Mycotoxins; D011728:Pyridones; C091237:sambutoxin