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• W2030350011 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." @default.
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• W2030350011 date "1983-01-01" @default.
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• W2030350011 title "Biomimetic total synthesis of (−)-codeine" @default.
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• W2030350011 doi "https://doi.org/10.1016/s0040-4020(01)91965-9" @default.
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