Total synthesis of natural (+)- [corrected] and ent-(-)-4-desacetoxy-6,7-dihydrovindorosine [corrected] and natural and ent-minovine: oxadiazole tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction.
Org Lett
; 7(4): 741-4, 2005 Feb 17.
Article
em En
| MEDLINE
| ID: mdl-15704939
ABSTRACT
Efficient and unusually concise total syntheses of both enantiomers of the Aspidosperma alkaloids 4-desacetoxy-6,7-dihydrovindorosine (12) and minovine (1) are detailed. A tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction of the 1,3,4-oxadiazole 8, in which three new rings, four new C-C bonds, and five stereocenters are formed, is a key step in the sequence. The availability of optically active material permitted an assessment of the enantiomeric integrity of minovine and the source of its reported unusual optical rotation. [Reaction see text]
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Alcaloides de Vinca
/
Alcaloides
Idioma:
En
Ano de publicação:
2005
Tipo de documento:
Article