Position of coordination of the lithium ion determines the regioselectivity of demethylations of 3,4-dimethoxymorphinans with L-selectride.
Org Lett
; 7(13): 2531-4, 2005 Jun 23.
Article
em En
| MEDLINE
| ID: mdl-15957883
ABSTRACT
[reaction see text] L-Selectride is an efficient agent for the 3-O-demethylation of opioids and is known to cleave the least hindered methoxyl group in a molecule. The treatment of a 3,4-dimethoxymorphinan containing a 6-ketal with L-Selectride gave selective 4-O-demethylation, rather than cleavage of the less hindered 3-methoxyl. In contrast, a 3,4-dimethoxymorphinan lacking a 6-ketal gave selective 3-O-demethylation, suggesting that the regiochemistry of L-Selectride-mediated O-demethylation can be manipulated through altering the position of coordination of the lithium ion.
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Base de dados:
MEDLINE
Assunto principal:
Lítio
/
Morfinanos
/
Entorpecentes
Idioma:
En
Ano de publicação:
2005
Tipo de documento:
Article