Toward the Synthesis of (‒)-Codeine by Chiral Auxiliary-Mediated Nitrone Cycloaddition

Desymmetrization of a p-quinone monoacetal by organocatalytic sulfa-Michael addition provided rapid access to a C-ring building block for a formal synthesis of (-)-codeine. By means of a diastereoselective 1,2-addition for A/C-ring union, an intramolecular nitrone cycloaddition for construction of the phenanthrene core, and a sulfoxide elimination, an enantiopure key intermediate of the authors' previous synthesis of racemic codeine was available in 12 steps from isovanillin.

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Toward the Synthesis of (‒)-Codeine by Chiral Auxiliary-Mediated Nitrone Cycloaddition

Cited by 4 publications

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Interpol review of controlled substances 2016–2019

Interpol review of controlled substances 2016–2019

Total Synthesis of (±)-Thebainone A by Intramolecular Nitrone Cycloaddition

Formal Synthesis of (−)-Codeine by Application of Temporary Thio Derivatization

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