A synthesis of 7.ALPHA.-methoxycephalosporins through selenenamides.

概要

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The o-nitrobenzeneselenenamides were oxidized with active manganese dioxide to give the irnines, which were converted to the 7α-methoxycephalosporins 3 by the reaction with lithium methoxide. The selenenamides 3 were acylated with phenoxyacetyl chloride to afford the desired cephamycin derivatives 4 via tertiary amide 5, which was not isolable. This methoxylation reaction was also carried out in penicillin series to give the desired 6α-methoxypenicillin 8 although the ring opening compound 9 was a major product. The difference between sulfenamides and selenenamides in their acylation reactions was discussed.
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