Total Synthesis of Penicyclone A Using a Double Grignard Reaction.
J Org Chem
; 87(23): 16054-16062, 2022 12 02.
Article
em En
| MEDLINE
| ID: mdl-36383733
ABSTRACT
We describe the first total synthesis of penicyclone A, a novel deep-sea fungus-derived polyketide, and a reevaluation of its antimicrobial activity. The synthesis of this unique spirolactone was achieved in 10 steps starting from a known d-ribose derivative. The key steps include a double Grignard reaction for the diastereoselective construction of the chiral tertiary alcohol intermediate, tandem oxidation/cyclization, and photooxygenation, followed by an oxidative rearrangement to introduce the enone functionality.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Ciclização
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2022
Tipo de documento:
Article
País de afiliação:
Croácia