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• W2014242022 abstract "A new synthetic strategy for the synthesis of the opiate and amaryllidaceae alkaloids emerges employing a Pd-catalyzed asymmetric allylic alkylation to set the stereochemistry. The pivotal tricyclic intermediate is available in six steps from 2-bromovanillin and the monoester of methyl 6-hydroxycyclohexene-1-carboxylate, the latter available from glutaraldehyde and the Emmons−Wadsworth−Horner phosphate reagent. This intermediate requires only two steps to convert to (−)-galanthamine. Using a Heck vinylation, we found that the fourth ring of codeine/morphine is formed. The final ring formation involves a novel visible light-promoted hydroamination. Thus, six steps are required to convert the pivotal tricyclic intermediate into codeine, which has been demethylated in high yield to morphine." @default.
• W2014242022 created "2016-06-24" @default.
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• W2014242022 date "2002-11-15" @default.
• W2014242022 modified "2023-10-03" @default.
• W2014242022 title "Enantioselective Synthesis of (−)-Codeine and (−)-Morphine" @default.
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• W2014242022 doi "https://doi.org/10.1021/ja0283394" @default.
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