Abstract
Bilirubin oxidation end products (BOXes) show significant physiological effects and are connected to severe diseases such as subarachnoid hemorrhage induced cerebral vasospasm. BOX B (2-(4-ethenyl-3-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide) was prepared via a five-step synthesis starting from methyl (4-bromo-3-methyl-5-oxofuran-2(5H)-ylidene)ethanoate that was vinylated and then reacted with NH4OAc, LiOH, (COCl)2, and finally with ammonia yielding Z-BOX B. Derivatives of Z-BOX A and Z-BOX B with [15N]labeled lactam rings were synthesized accordingly.
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