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

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 J.
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
Affiliation
Universidad de Alcalá. Departamento de 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.).
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
CTQ2005/011060/BQU (Ministerio de Ciencia e Innovación)
CCG-UAH/SAL-0660 (Universidad de Alcalá-UAH)
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
(c) Elsevier, 2008
Access rights
info:eu-repo/semantics/openAccess
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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.
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