Palladium-mediated C-N, C-C, and C-O functionalization of azolopyrimidines: a new total synthesis of variolin B

  View metrics of use
Utilizar EndNote Import
Authors
Baeza García, AlejandroUniversity of Alcalá Author; Mendiola Serena, JavierUniversity of Alcalá Author; Burgos García, CarolinaUniversity of Alcalá Author; Álvarez-Builla Gómez, JulioUniversity of Alcalá Author; Vaquero López, Juan JoséUniversity of Alcalá Author
Identifiers
Permanent link (URI): http://hdl.handle.net/10017/2653
DOI: 10.1016/j.tetlet.2008.04.063
ISSN: 0040-4039
Publisher
Elsevier
Date
2008
Academic Departments
Universidad de Alcalá. Departamento de Química Orgánica
Teaching unit
Unidad docente Química Orgánica
Funders
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
Bibliographic citation
Tetrahedron Letters, 2008, v. 49, n. 25, p. 4073-4077
Keywords
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
Project
info:eu-repo/grantAgreement/MICINN//CTQ2005%2F011060%2FBQU/ES//
info:eu-repo/grantAgreement/UAH//CCG-UAH%2FSAL-0660/ES//
Document type
info:eu-repo/semantics/article
Version
info:eu-repo/semantics/publishedVersion
Publisher's version
http://dx.doi.org/10.1016/j.tetlet.2008.04.063
Rights
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
Access rights
info:eu-repo/semantics/openAccess
Abstract
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.

Show full item record

Files in this item
Collections
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
Este ítem está sujeto a una licencia Creative Commons.