Remarkable switch of regioselectivity in Diels-Alder reaction: divergent total synthesis of borreverine, caulindoles, and flinderoles.
Org Lett
; 16(10): 2764-7, 2014 May 16.
Article
em En
| MEDLINE
| ID: mdl-24797220
ABSTRACT
Switchable reaction patterns of dimerization of indole substituted butadienes via a Lewis acid and thermal activation are reported. While under acidic conditions dimerization occurred around the internal double bond of the dienophile, a complete switch of regioselectivity was observed under thermal conditions, where dimerization occurred around the terminal double bond of the dienophile. This switch of regioselectivity was further exploited for the divergent total synthesis of structurally diverse indole alkaloid natural products.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Produtos Biológicos
/
Alcaloides Indólicos
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Alcaloides
/
Indóis
Idioma:
En
Ano de publicação:
2014
Tipo de documento:
Article