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Synfacts 2009(2): 0126-0126  
DOI: 10.1055/s-0028-1087602
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (±)-Codeine

Contributor(s): Philip Kocienski, Indu Dager
M. Varin, E. Barré, B. Iorga*, C. Guillou*
Institut de Chimie des Substances Naturelles, Gif-sur-Yvette, France
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Publication History

Publication Date:
22 January 2009 (online)

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Significance

Key steps in this diastereoselective synthesis of ()-codeine are (1) an intramolecular Heck reaction (A → B) and (2) the stereoselective introduction of the C-14 substituent via an ­Eschenmoser-Claisen rearrangement (C → E).