Total syntheses of (+)- and (-)-cacospongionolide B: new insight into structural requirements for phospholipase A(2) inhibition.
J Am Chem Soc
; 124(39): 11584-5, 2002 Oct 02.
Article
em En
| MEDLINE
| ID: mdl-12296709
ABSTRACT
The first total synthesis of the antiinflammatory marine sponge metabolite (+)-cacospongionolide B has been accomplished in 12 linear steps. The pivotal transformations include a three-step sequence coupling the two main regions of the natural product as well as generating the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that cacospongionolide B has an enantiospecific interaction with the enzyme that is independent of the gamma-hydroxybutenolide moiety.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Fosfolipases A
/
Piranos
/
4-Butirolactona
/
Inibidores Enzimáticos
Idioma:
En
Ano de publicação:
2002
Tipo de documento:
Article