alpha,beta-Dibenzyl-gamma-butyrolactone lignan alcohols: total synthesis of (+/-)-7'-hydroxyenterolactone, (+/-)-7'-hydroxymatairesinol and (+/-)-8-hydroxyenterolactone.
Steroids
; 66(10): 777-84, 2001 Oct.
Article
en En
| MEDLINE
| ID: mdl-11522341
ABSTRACT
Two trans-alpha,beta-dibenzyl-gamma-butyrolactone lignans carrying a hydroxyl group at the beta-benzylic carbon atom and a alpha-hydroxy alpha,beta-dibenzyl-gamma-butyrolactone lignan were synthesized in racemic form using the tandem conjugate addition reaction to construct the basic lignan skeleton. Subsequent reaction steps involved either a catalytic reduction of the regenerated keto group to the alcohol, or a hydrogenolysis to benzylic methylene followed by lactone enolate formation and oxidation to give the alpha-hydroxybutyrolactones. These procedures were applied for the synthesis of 7'-hydroxyenterolactones and 7'-hydroxymatairesinols, and 8-hydroxyenterolactones, respectively. The diastereomeric mixtures of these compounds were separated either by HPLC techniques or column chromatography and the structures were elucidated using NMR spectroscopy.
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Bases de datos:
MEDLINE
Asunto principal:
Extractos Vegetales
/
Lignanos
/
Alcoholes
/
Lactonas
Idioma:
En
Revista:
Steroids
Año:
2001
Tipo del documento:
Article
País de afiliación:
Finlandia