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Diastereoselective Total Synthesis of (±)‐Codeine
Author(s) -
Varin Marie,
Barré Elvina,
Iorga Bogdan,
Guillou Catherine
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800744
Subject(s) - codeine , claisen rearrangement , chemistry , stereochemistry , tricyclic , combinatorial chemistry , morphine , pharmacology , medicine
The value of a tricyclic spirocyclohexadienone intermediate has been illustrated again in the diastereoselective synthesis of (±)‐codeine. From this useful intermediate, the formation of the B and D rings of codeine involved a Claisen–Eschenmoser rearrangement as a key step.