Tetrahedron Letters p. 8379 - 8382 (2007)
Update date:2022-08-02
Topics:
Ferrara, Marco
Crescenzi, Benedetta
Donghi, Monica
Muraglia, Ester
Nizi, Emanuela
Pesci, Silvia
Summa, Vincenzo
Gardelli, Cristina
The hexahydropyrimido[1,2-a]azepine-2-carboxamide derivative 1 could be obtained by three synthetic strategies, which allowed access to multigram amounts of material of high purity and ee. Two strategies involved alternative approaches to the bicyclic pyrimidone core, with the most efficient one being a two-step sequence from commercially available starting materials exploiting a little precedented cyclisation reaction. The remaining steps to 1 included an efficient crystallisation of an intermediate as a single stereoisomer. An alternative strategy employing a chiral starting material led to products of low optical purity but allowed the assignment of the configuration of the stereogenic centre of 1.
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