Hughes, Rachael A.; Thompson, Stewart P.; Alcaraz, Lilian; Moody, Christopher J. published the artcile< Total Synthesis of the Thiopeptide Antibiotic Amythiamicin D>, SDS of cas: 31825-95-3, the main research area is amythiamicin antibiotic thiopeptide total synthesis; pyridine trisubstituted preparation hetero Diels Alder reaction acetylenamine ethoxyazadiene.
The thiopeptide (or thiostrepton) antibiotics are a class of sulfur containing highly modified cyclic peptides with interesting biol. properties, including reported activity against MRSA and malaria. This work describes the total synthesis of the thiopeptide natural product amythiamicin D (I), and the key step is a biosynthesis-inspired hetero-Diels-Alder route to the pyridine core of the thiopeptide. Preliminary studies using a range of serine-derived 1-ethoxy-2-azadienes established that hetero-Diels-Alder reaction with N-acetylenamines proceeded efficiently under microwave irradiation to give 2,3,6-trisubstituted pyridines. The thiazole building blocks of the antibiotic were obtained by either classical Hantzsch reactions or by dirhodium(II)-catalyzed chemoselective carbene N-H insertion followed by thionation, and were combined to give the bis-thiazole that forms the left-hand fragment of the antibiotic. The key Diels-Alder reaction of a tris-thiazolylazadiene II with benzyl 2-(1-acetylaminoethenyl)thiazole-4-carboxylate gave the core tetrathiazolyl pyridine III, which was elaborated into the natural product by successive incorporation of glycine and bis-thiazole fragments followed by macrocyclization.
Journal of the American Chemical Society published new progress about Cyclic peptides Role: SPN (Synthetic Preparation), PREP (Preparation) (thiopeptides). 31825-95-3 belongs to class thiazole, and the molecular formula is C5H6N2OS, SDS of cas: 31825-95-3.
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica