Flexible and Convergent Enantioselective Total Synthesis of (R)-Juglanaloids A and B: Two Phthalide Spiro Alkaloids with Potential Alzheimer's Disease Inhibitory Activity.
J Org Chem
; 89(10): 7255-7262, 2024 May 17.
Article
em En
| MEDLINE
| ID: mdl-38718382
ABSTRACT
Juglanaloids A and B are recently isolated natural products characterized by an unprecedented spiro bicyclic isobenzofuranone-tetrahydrobenzazepinone framework and a promising antiamyloid activity. Here reported is a straightforward convergent total synthesis of these natural products, which were obtained in high enantiomeric purity (94% and >99% ee for juglanaloids A and B, respectively) through an eight-step longest linear sequence, based on an efficient and reliable enantioselective phase-transfer-catalyzed alkylation step. Considering the interesting biological activity of juglanaloids, this convenient, highly enantioselective, flexible, and predictable synthetic strategy promises to be a powerful tool for accessing potentially bioactive spiro bicyclic phthalide-tetrahydrobenzazepinone derivatives.
Texto completo:
1
Bases de dados:
MEDLINE
Assunto principal:
Compostos de Espiro
/
Alcaloides
/
Doença de Alzheimer
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2024
Tipo de documento:
Article
País de afiliação:
Itália