A new approach to (-)-swainsonine by ruthenium-catalyzed ring rearrangement.
J Org Chem
; 67(12): 4325-9, 2002 Jun 14.
Article
em En
| MEDLINE
| ID: mdl-12054970
ABSTRACT
A new enantioselective synthesis of the idolizidine alkaloid (-)-swainsonine 1 in 40% overall yield starting from the known oxazolidinone 6 is described. Throughout the synthesis, the high efficiency of metal-catalyzed reactions is illustrated. The key step is a new ruthenium-catalyzed metathesis rearrangement reaction. In this ring-closing/ring-opening tandem process, stereocenters are transferred from a ring to the olefinic side chain of the formed heterocycle. The metathesis precursor was obtained by palladium-catalyzed desymmetrization of cyclopentenediol. The synthesis was completed by functionalization of the terminal double bond, cyclization of the second ring, and diastereoselective dihydroxylation.
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Base de dados:
MEDLINE
Assunto principal:
Rutênio
/
Química Orgânica
/
Swainsonina
/
Alcaloides
Idioma:
En
Ano de publicação:
2002
Tipo de documento:
Article