Total synthesis of the interleukin-1beta converting enzyme inhibitor EI-1941-2 using tandem oxa-electrocyclization/oxidation1.
[reaction: see text] The total synthesis of the interleukin-1beta converting enzyme inhibitor EI-1941-2 was achieved utilizing tandem oxidation/oxa-electrocyclization/oxidation to access a key alpha-pyrone intermediate. Support for the tandem reaction mechanism was obtained by evaluation of a stepwise oxidation protocol.
Kleinke
Andrew S
AS
Department of Chemistry, Boston University, Massachusetts 02215, USA.
Li
Chaomin
C
Rabasso
Nicolas
N
Porco
John A
JA
D003500:Cyclization; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000494:pharmacology; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D015394:Molecular Structure; D010084:Oxidation-Reduction; D015843:Serpins / Q000138:chemical synthesis* / Q000494:pharmacology; D014764:Viral Proteins / Q000138:chemical synthesis* / Q000494:pharmacology
D003512:Cyclohexanones; C476114:EI-1941-2; D004852:Epoxy Compounds; D015843:Serpins; D014764:Viral Proteins; C074641:interleukin-1beta-converting enzyme inhibitor