69295-27-8Relevant articles and documents
An alternative approach to the synthesis of the three fragments of anachelin H
Gamba-Sánchez, Diego,Garzón-Posse, Fabián,Prunet, Jo?lle
, p. 2702 - 2715 (2020/04/17)
The synthesis of the fully protected peptide, polyketide and alkaloid fragments of anachelin H is presented. The peptide fragment was prepared using a liquid phase peptide synthesis; the polyketide fragment was synthetized using a cross metathesis and an intramolecular oxa-Michael reaction as the key steps to introduce the desired stereochemistry; finally, the alkaloid fragment was obtained by an oxidative cyclization of a catechol derivative using potassium ferricyanide. The synthesis of all fragments was based on the use of natural amino acids as sources of asymmetry. The independent synthesis of the three fragments should allow more efficient biological studies on the fragments instead of the whole natural product. Experiments to illustrate the coupling of fragments and the effectiveness of the convergent strategy are also described.
Synthesis of the Chromophore of Pseudobactin, a Fluorescent Siderophore from Pseudomonas
Kolasa, Teodozyj,Miller, Marvin J.
, p. 4246 - 4255 (2007/10/02)
Protected forms of dihydroxyphenylalanine (DOPA) were converted to the corresponding dihydroquinolin-2-ones 13 by nitration and reductive cyclization.Subsequent N-alkylation with α-halo-γ-aminobutyric acid derivatives provided the carbon framework 12 for the chromophore of pseudobactin.Conversion to protected forms of the fluorescent chromophore 5 was accomplished by reaction of 12 with Lawesson's reagent to produce the corresponding thioamide which was cyclized by reaction with mercuric acetate.
