Synthesis of Orthogonally N-Protected, C-4 Functionalized Cyclic Guanidines from L-Serine

Diego Silva , Edmilson Maria , Rosa Suárez Ordóñez , Josiane Thierry (1) , Kevin Cariou (1) , Robert Dodd

1 ICSN - Institut de Chimie des Substances Naturelles

A straightforward and efficient preparation of 5-membered cyclic guanidines bearing an ester, a hydroxymethyl or a Weinreb amide functional group at C-4 is described from L-serine. The novel synthetic route provides cyclic guanidines in which the three nitrogen atoms are orthogonally protected making them highly suitable for further transformations into natural products or their analogues via the introduced functional groups.

Mots clés: cyclic guanidine; amino acid; azide; orthogonal protection; Weinreb amide

Domaines: Chimie organique

Diego Silva, Edmilson Maria, Rosa Suárez Ordóñez, Josiane Thierry, Kevin Cariou, et al.. Synthesis of Orthogonally N-Protected, C-4 Functionalized Cyclic Guanidines from L-Serine. SYNLETT, 2017, 28 (07), pp.815-818. ⟨10.1055/s-0036-1589935⟩. ⟨hal-02307213⟩