Abstract
The opium alkaloid (−)-codeine was synthesized in eight steps from (±)-N-norreticuline R-(−)-norreticuline, obtained by resolution, was converted to (R)-N-trifluoroacetyl-6'-bromonorreticuline and the latter was subjected to phenolic oxidative coupling with a variety of aryliodoso complexes in dichloromethane. N-Trifluoroacetyl-1-bromonorsalutaridine prepared by this means was transformed to 1-bromosalutaridinol (as a mixture of epimers), and the latter were dehydrated separately to 1-bromothebaine with dimethylformamide dineopentyl acetal. Hydrolysis to 1-bromocodeinone, followed by reductive removal of Br with LAH, afforded (−)-codeine.
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