Stereoselective Total Synthesis of Aspergillide A: A Visible Light-Mediated Photoredox Access to the Trisubstituted Tetrahydropyran Core.
J Org Chem
; 84(18): 11848-11855, 2019 09 20.
Article
em En
| MEDLINE
| ID: mdl-31416311
A stereoselective total synthesis of natural product aspergillide A is reported. The adopted strategy relies on the direct access to the key tetrahydropyran core through a visible light-mediated photoredox reaction from an allylic alcohol and iodoacetic acid. In a single manipulation, a γ-iodo-δ-valerolactone is obtained through an atom transfer radical addition followed by in situ acid-catalyzed lactonization. The obtained lactone possesses three functionalized sites, which were seized to link the required substituents in the final product and thus completing the total synthesis of aspergillide A.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Piranos
/
Macrolídeos
/
Técnicas de Química Sintética
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2019
Tipo de documento:
Article
País de afiliação:
México
País de publicação:
Estados Unidos