Total Synthesis of Homo- and Heterodimeric Bispyrrolidinoindoline Dioxopiperazine Natural Products
Andrea Areal, Marta Domínguez, Pim Vendrig, Susana Álvarez, Rosana Álvarez, Ángel R. de Lera
Abstract
), has been carried out starting from the corresponding bispyrrolidinoindolines derived from tryptophan. Our efforts to synthesize all possible diastereomers of the natural ditryptoleucine isolates uncovered structural factors that determine the rate and efficiency of dioxopiperazine ring formation, leading in some cases to mixtures of diastereomers by concomitant epimerization, to the formation of their putative monomeric dioxopiperazine dipeptide biogenetic precursors, and to the alternative formation of a dimer with a fused 1,3,5-triazepan-6-one heterocycle.
Topics & Concepts
DiastereomerStereochemistryEpimerDimerDipeptideMonomerBiologyStereoisomerismChemistryBiochemistryOrganic chemistryAmino acidCatalysisPolymerSynthesis and bioactivity of alkaloidsSynthesis and Biological ActivityMicrobial Natural Products and Biosynthesis