Flexible strategy for the synthesis of pyrrolizidine alkaloids.
Org Lett
; 10(16): 3615-8, 2008 Aug 21.
Article
em En
| MEDLINE
| ID: mdl-18636741
ABSTRACT
A general strategy for the production of pyrrolizidine alkaloids is described, starting from intermediate (+)-9. The key features are diastereoselective dihydroxylation, inversion at the ring junction by hydroboration of an enamine, and ring closure to form the bicyclo ring system. This route is attractive because of its brevity and versatility; four natural products were prepared with differing stereochemistry and substitution patterns. Finally, this work allowed assignment of the absolute stereochemistry of 2,3,7-triepiaustraline and hyacinthacine A 7.
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1
Base de dados:
MEDLINE
Assunto principal:
Alcaloides de Pirrolizidina
Idioma:
En
Ano de publicação:
2008
Tipo de documento:
Article