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Updated: Sep 24, 2025

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
First total synthesis of versicotide A, B and C
Laura Posada1,2, Danilo Davyt1, Gloria Serra1
1Química Farmacéutica, Departamento de Química Orgánica, Facultad de Química, Universidad de la República General Flores 2124 CC1157 Montevideo Uruguay gserra@fq.edu.uy.
Abstract:
The syntheses of versicotides A-C, natural products containing anthranilic acid and NMe-Ala, were achieved by solid phase peptide synthesis on 2-chlorotrityl resin followed by solution phase macrocyclization. Using an oxyma additive, the difficult coupling reactions to the deactivated aromatic amine of o-aminobenzoic acid, were performed in high yield, avoiding anthranilic rearrangements or side reactions.
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