Short Scalable Route to Apiaceae Sesquiterpene Scaffolds: Total Synthesis of 4-epi-Epiguaidiol A.
Org Lett
; 24(46): 8476-8480, 2022 11 25.
Article
em En
| MEDLINE
| ID: mdl-36264031
ABSTRACT
The oxy-Cope/ene reaction cascade to form a locked elemane conformer allows the short scalable synthesis of versatile Apiaceae scaffolds. The divergent fate of the obtained macrocyclic germacrane is surveyed under cationic and dioxygen-induced Prins-type reaction conditions to allow the diastereoselective synthesis of oxidized Apiaceae guaiane congeners and the total synthesis of 4-epi-epiguaidiol A. Additionally, the unprecedented reduction of a hydrogen-bond-biased guaiane substrate permits the chemoselective synthesis of desoxo-jungiaguaiane.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Sesquiterpenos
/
Apiaceae
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article