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Synfacts 2010(12): 1343-1343  
DOI: 10.1055/s-0030-1258954
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Pyridopyrrolopyrimidines. Total Synthesis of Varioline B and Deoxyvariolin B

Contributor(s): Victor Snieckus, Matthew O. Kitching
A. Baeza, J. Mendiola, C. Burgos, J. Alvares-Builla, J. J. Vaquero*
Universidad de Alcalá, Alcalá de Henares, Spain
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Publication History

Publication Date:
22 November 2010 (online)

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Significance

Reported is the synthesis of pyridopyrrolopyrimidines via the cyclization of 2-bromomethyl azaindoles with TosMIC. Attempts to further elaborate intermediate A into the variolins, however, were unsuccessful. The problem was solved by the use of tosylmethylimines (B and D). Screens of reaction conditions allowed the synthesis of F, which could ultimately be transformed into the variolin natural products.