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Total Synthesis of rac ‐Salutaridine and Sinoacutine ((−)‐salutaridine)—A Novel Route to the Morphine Skeleton
Author(s) -
Ludwig Wolfgang,
Schäfer Hans J.
Publication year - 1986
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198610251
Subject(s) - morphine , skeleton (computer programming) , chemistry , residue (chemistry) , total synthesis , stereochemistry , pharmacology , organic chemistry , biology , anatomy
(Biomimetic) C6′C4 coupling is essential for formation of the morphine skeleton . It was accomplished by using a precursor 1 containing a tetrahydrogenated, substituted benzyl residue. The product 2 (salutaridine) can be converted into morphine (TBS = Si t BuMe 2 , R 1 = benzyl).
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