Stereocontrolled synthesis of triazacyclopenta[cd]pentalenes by intramolecular 1,3-dipolar cycloaddition reactions of azomethine imines.
J Org Chem
; 67(22): 7880-3, 2002 Nov 01.
Article
em En
| MEDLINE
| ID: mdl-12398520
ABSTRACT
The construction of triazacyclopenta[cd]pentalene diesters 6 by the reaction of dihydropyrrole alpha-ketoesters 3 with acylated hydrazines was evaluated further as a potential central strategic step in the total syntheses of complex guanidine alkaloids such as palau'amine and styloguanidine. Successful cyclocondensations were realized with acid-stable 2,2,2-trichloroethyl carbazate and thiosemicarbazide, but not tert-butyl carbazate. The substituent on the pyrrolidine nitrogen can be alkoxycarbonyl, sulfonyl, or an N-alkyl-2-acylpyrrole group. Siloxy substitution at C1 of the alpha-ketoester side chain is also tolerated.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Ciclopentanos
/
Iminas
Idioma:
En
Ano de publicação:
2002
Tipo de documento:
Article