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Synthesis and stereochemistry of the (9 S ,13 S ,14 S )‐3‐hydroxy‐17‐methylmorphinan‐10‐ols
Author(s) -
Mohacsi Erno,
O'Brien Jay P.
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280117
Subject(s) - chemistry , stereochemistry , demethylation , biochemistry , gene expression , dna methylation , gene
O ‐Demethylation of (9 S ,13 S ,14 S )‐3‐methoxy‐17‐methylmorphinan‐10‐one ( 2 ) to (9 S ,13 S ,14 S )‐3‐hydroxy‐17‐methylmorphinan‐10‐one ( 3 ) and reduction of 3 to 10α‐ and 10β‐hydroxylated morphinans 4 and 5 , are described. The stereochemistry of these epimeric alcohols was established on the bases of 1 H nmr data.