The viability of nitrone-alkene (3 + 2) cycloadditions in alkaloid biosynthesis.
J Org Chem
; 79(1): 432-5, 2014 Jan 03.
Article
em En
| MEDLINE
| ID: mdl-24236542
ABSTRACT
Although evidence has mounted in recent years for the biosynthetic relevance of [4 + 2] cycloaddition reactions, other cycloadditions have received much less attention. Herein we used density functional theory (DFT) calculations to assess the viability of nitrone-alkene (3 + 2) cycloaddition reactions proposed to occur during the biosynthesis of several alkaloid natural products (flueggines and virosaines). The results of our calculations indicate that these reactions have low enough intrinsic barriers and diastereoselectivity that they can proceed without enzymatic intervention.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Produtos Biológicos
/
Alcaloides
/
Alcenos
/
Óxidos de Nitrogênio
Idioma:
En
Ano de publicação:
2014
Tipo de documento:
Article