Total Syntheses of Marrubiin and Related Labdane Diterpene Lactones.
Molecules
; 25(7)2020 Apr 01.
Article
em En
| MEDLINE
| ID: mdl-32244661
ABSTRACT
Total syntheses of the labdane diterpene lactones marrubiin, marrulibacetal, desertine, marrulibacetal A, marrubasch F, cyllenine C, marrulanic acid, and marrulactone are described. The trans-decalin moiety of these molecules was constructed in a stereoselective manner by a Pauson-Khand reaction, and the resultant cyclopentenone was oxidatively cleaved for formation of the lactone ring. Elongation of the side chain at C9 was achieved by an epoxide-opening reaction with a variety of nucleophiles, and the functional group manipulations completed the syntheses of these natural products. Stereochemistries of desertine could be established by the transformations.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Diterpenos
/
Técnicas de Química Sintética
/
Lactonas
Idioma:
En
Revista:
Molecules
Ano de publicação:
2020
Tipo de documento:
Article