Palladium-mediated C-N, C-C, and C-O functionalization of azolopyrimidines: a new total synthesis of variolin B
Autores
Baeza García, Alejandro; Mendiola Serena, Javier; Burgos García, Carolina; Álvarez-Builla Gómez, Julio; Vaquero López, Juan J.Identificadores
Enlace permanente (URI): http://hdl.handle.net/10017/2653DOI: 10.1016/j.tetlet.2008.04.063
ISSN: 0040-4039
Editor
Elsevier
Fecha de publicación
2008Patrocinadores
The authors acknowledge financial support from the
Spanish Ministerio de Educación y Ciencia (project
CTQ2005/011060/BQU), Comunidad de Madrid (CAM),
and Universidad de Alcalá (UAH) (project CCG-UAH/
SAL-0660) and a grant from the Ministerio de Educación
y Ciencia (A.B.).
Ministerio de Ciencia e Innovación
Universidad de Alcalá
Cita bibliográfica
Tetrahedron Letters, 2008, v. 49, n. 25, p. 4073-4077
Palabras clave
Variolin B
Total synthesis
Palladium-mediated C-N, C-C and C-O; pyrido[3 ',2 ': 4,5]pyrrolo[1,2-c]pyrimidine
N-tosylmethyl dichloro-formimide
Sponge kirkpatrickia-varialosa
Deoxyvariolin-B
Bond formation
Alkaloids
Core
Derivatives
Ethers
Chemistry, Organic
Proyectos
info:eu-repo/grantAgreement/MICINN//CTQ2005%2F011060%2FBQU/ES//
info:eu-repo/grantAgreement/UAH//CCG-UAH%2FSAL-0660/ES//
Tipo de documento
info:eu-repo/semantics/article
Versión
info:eu-repo/semantics/publishedVersion
Versión del editor
http://dx.doi.org/10.1016/j.tetlet.2008.04.063Derechos
(c) Elsevier, 2008
Derechos de acceso
info:eu-repo/semantics/openAccess
Resumen
A new total synthesis of the alkaloid variolin B is achieved by a selective and sequential palladium-mediated functionalization of a
trihalo-substituted pyrido[30
,20
:4,5]pyrrolo[1,2-c]pyrimidine. This intermediate is obtained by a new heterocyclization reaction between
an appropriate bromomethyl azaindole and N-tosylmethyl dichloroformimide. The methodology may be effective for the synthesis of
some analogs by substitution on the relatively unexplored C4 and C9 positions of the alkaloid.
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