Divergent Total Synthesis of Euphoranginolâ
C, Euphoranginoneâ
D, ent-Trachyloban-3ß-ol, ent-Trachyloban-3-one, Excoecarinâ
E, and ent-16α-Hydroxy-atisane-3-one.
Angew Chem Int Ed Engl
; 59(45): 19919-19923, 2020 11 02.
Article
em En
| MEDLINE
| ID: mdl-32696611
ABSTRACT
A divergent synthetic approach to biogenetically related diterpenoids such as ent-kauranes, ent-trachylobanes, ent-beyerane, and ent-atisane has been developed. The unified synthetic route involves the De Mayo reaction to rapidly generate the bicyclo[3.2.1]-octane moiety of ent-kaurane. The key reactions also include bioinspired nucleophilic cyclopropanation generating the [3.2.1.02,7 ]-tricyclic core of ent-trachylobane and regioselective cyclopropane fragmentation furnishing ent-beyerane and ent-atisane through the nucleophilic attack and protonation of the cyclopropane ring. This strategy enables the asymmetric total syntheses of six diterpenoids from the commercially available geraniol.
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Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article