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Journals and Conferences
Alkaloids containing a central bicyclo[n.2.2]piperazinedione (diketopiperazine, DKP, n 2) ring system, bridged at positions 3 and 6, constitute an ever-growing class of secondary metabolites. DKPs 1, biosynthesized from amino acids either by nonribosomal peptide synthases (NRPS) or by tRNA-dependent enzymes called cyclodipeptide synthases (CDPS), are the… (More)
Green fluorescent protein (GFP) and homologous proteins possess a unique pathway of chromophore formation based on autocatalytic modification of their own amino acid residues. Green-to-red photoconvertible fluorescent protein Kaede carries His-Tyr-Gly chromophore-forming triad. Here, we describe synthesis of Kaede red chromophore… (More)
A conceptually new and unified approach to diverse bridged diketopiperazines (DKPs) with widely variable ring sizes was developed by taking advantage of the persistent radical effect. This method enables synthesis of the core structures of bridged DKP alkaloids and was applied to a formal synthesis of the antibiotic bicyclomycin.
The most advanced approach, so far, to the asperparalines is developed. Consecutive oxidative and reductive radical cyclizations serve as the key steps to stereoselectively access the complex fully elaborated skeleton containing the cyclopentane and spiro-succinimide units.
A novel approach to the diazabicyclo[2.2.2]octane core of prenylated bridged diketopiperazine alkaloids is described by direct oxidative cyclizations of functionalized diketopiperazines mediated by ferrocenium hexafluorophosphate or the Mn(OAc)3•2H2O/Cu(OTf)2 system. Divergent reaction pathways take place depending on the substitution pattern of the… (More)