Efficient syntheses of oncinotine and neooncinotine.
J Org Chem
; 69(18): 6094-9, 2004 Sep 03.
Article
em En
| MEDLINE
| ID: mdl-15373494
ABSTRACT
We have synthesized two natural alkaloids, oncinotine (1) and neooncinotine (2), by means of efficient ring-closing metathesis (RCM) reactions. The required dienes for RCM were assembled from three basic components 2-allylpiperidine (5), 9-decenoic acid (6), and diamines 7. We developed two different methods to achieve the linkage the Michael addition of acrylamide and two amidations of succinic anhydride. The Grubbs catalyst was used to form the 17- and 18-membered lactams in 50% and 68% yields, respectively.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Alcaloides
/
Lactamas
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2004
Tipo de documento:
Article
País de publicação:
EEUU
/
ESTADOS UNIDOS
/
ESTADOS UNIDOS DA AMERICA
/
EUA
/
UNITED STATES
/
UNITED STATES OF AMERICA
/
US
/
USA