A short total synthesis of aureothin and N-acetylaureothamine.
The total synthesis of the nitrophenyl pyrones, (+/-)-aureothin and (+/-)-N-acetylaureothamine, starting from known 2-ethyl-6-methoxy-3,5-dimethyl-4H-pyran-4-one are described. The key steps involved in the synthesis are the construction of the tetrahydrofuran motif using a palladium-catalyzed cycloaddition and the ruthenium-catalyzed cross-metathesis reaction of an alkenyl boronic ester. [reaction: see text]
Jacobsen
Mikkel F
MF
Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, United Kingdom.
Moses
John E
JE
Adlington
Robert M
RM
Baldwin
Jack E
JE
D000107:Acetylation; D000588:Amines / Q000138:chemical synthesis; D002867:Chromones / Q000138:chemical synthesis / Q000737:chemistry; D007202:Indicators and Reagents; D008958:Models, Molecular; D013237:Stereoisomerism
D000588:Amines; D002867:Chromones; D007202:Indicators and Reagents; C012198:aureothin