Formation of β-lactams from 3-phenylthiopropionamide derivatives. A possible model for penicillin biosynthesis
The Cu-catalysed reaction of the substituted 3-phenylthiopropianamide with di-t-butyl peroxide gives the β-lactam via oxidative cyclisation of the α-thioalkyl radical. Similar reactions of the propionamides with t-butyl perbenzoate give benzoates which can be readily converted into the β-lactams, but neither β-lactams nor benzoates can be obtained from the thiazepines. Dimethyl disulfide is benzoyloxylated on treatment with t-butyl perbenzoate. The relevance of these results to penicillin biosynthesis is discussed.
Beckwith,Easton
p. 3995 - 4001
(2007/10/02)
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