Long-chain 2H-azirines with heterogeneous terminal halogenation from the marine sponge Dysidea fragilis.
J Org Chem
; 73(7): 2592-7, 2008 Apr 04.
Article
em En
| MEDLINE
| ID: mdl-18321120
ABSTRACT
Three new omega-halogenated long-chain 2H-azirines were isolated from the sponge Dysidea fragilis. Their structures revealed heterogeneity in both the composition of the terminal 1,1-dihalo-vinyl group and enantiomeric ratios at C2 of the azirine-2-carboxylate ester terminus. Azirine-2-carboxylate esters were shown to racemize spontaneously. A hypothesis is proposed for the biosynthesis of the azirinecarboxylate family of natural products that involves enzyme-catalyzed free radical halogenation followed by elimination of hydrohalic acid.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Azirinas
/
Fatores Biológicos
/
Dysidea
Idioma:
En
Ano de publicação:
2008
Tipo de documento:
Article