Oxa-Michael-based divergent synthesis of artificial glutamate analogs.
RSC Adv
; 12(34): 22175-22179, 2022 Aug 04.
Article
em En
| MEDLINE
| ID: mdl-36043066
ABSTRACT
Herein we report stereoselective generation of two skeletons, 1,3-dioxane and tetrahydropyranol, by oxa-Michael reaction as the key reaction from δ-hydroxyenone. The construction of the 1,3-dioxane skeleton, achieved through hemiacetal formation followed by oxa-Michael reaction from δ-hydroxyenone, was exploited to access structurally diverse heterotricyclic artificial glutamate analogs. On the other hand, formation of a novel tetrahydro-2H-pyranol skeleton was accomplished by the inverse reaction order oxa-Michael reaction followed by hemiacetal formation. Thus, this study succeeded in showing that structural diversity in a compound collection can be acquired by interchanging the order of just two reactions. Among the skeletally diverse, heterotricyclic artificial glutamate analogs synthesized in this study, a neuronally active compound named TKM-50 was discovered in the mice in vivo assay.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
RSC Adv
Ano de publicação:
2022
Tipo de documento:
Article