Protecting group free enantiospecific total syntheses of structurally diverse natural products of the tetrahydrocannabinoid family.
Chem Commun (Camb)
; 51(14): 2871-3, 2015 Feb 18.
Article
em En
| MEDLINE
| ID: mdl-25582920
ABSTRACT
A simple, highly diastereoselective, Lewis acid catalyzed Friedel-Crafts coupling of a cyclic allylic alcohol with resorcinol derivatives has been developed. The method was applied for the enantiospecific total syntheses of structurally diverse natural products such as machaeriol-D, Δ(8)-THC, Δ(9)-THC, epi-perrottetinene and their analogues. Synthesis of both natural products and their enantiomers has been achieved with high atom economy, in a protecting group free manner and in less than 6 steps, the longest linear sequence, in a very good overall yield starting from R-(+) and S-(-)-limonene.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Chem Commun (Camb)
Ano de publicação:
2015
Tipo de documento:
Article