Abstract
AbstractThebaine (1) was converted into N‐formylnorthebaine (4) via N‐demethylation using diethyl azodicarboxylate followed by treatment with ethyl formate. Diels‐Alder reaction of 4 with nitroethene yielded 5 exclusively with the 6α,14α‐etheno bridge and the nitro group in the 7α‐position. Hydrolysis of 5 and methylation then gave 7, the nitroethene addition product of thebaine. Reduction of 5 and 7 with aluminium amalgam gave the corresponding 7α‐amines 11 and 8, respectively. Reduction of 7 with formamidinesulfinic acid or with lithium aluminium hydride gave only the oxime 9.
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