Formal syntheses of (±)-platensimycin and (±)-platencin via a dual-mode Lewis acid induced cascade cyclization approach.
J Org Chem
; 78(16): 7912-29, 2013 Aug 16.
Article
em En
| MEDLINE
| ID: mdl-23859063
ABSTRACT
A mild and efficient dual-mode Lewis acid induced Diels-Alder (DA)/carbocyclization cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenoids in one pot with the aid of a theoretical study on the π,σ-Lewis acidities of a variety of Lewis acids. With ZnBr2 as the dual-mode Lewis acid, a series of substituted enones and dienes underwent DA/carbocyclization cascade cyclization reaction smoothly at room temperature and provided the tricyclic cyclized products in one pot with good yields and high diastereoselectivity. The tricyclic cyclized product has been successfully utilized as a common intermediate for formal syntheses of (±)-platensimycin and (±)-platencin.
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Base de dados:
MEDLINE
Assunto principal:
Compostos Policíclicos
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Adamantano
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Ácidos de Lewis
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Aminobenzoatos
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Aminofenóis
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Anilidas
Idioma:
En
Ano de publicação:
2013
Tipo de documento:
Article