177326-54-4

Upstream product

• 23876-13-3 (2-methyl-3-nitrophenyl)methanol 
• 1010733-23-9 ethyl 3-methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1H-indole-2-carboxylate 
• 177326-62-4 ethyl 2-nitro-6-(2-tetrahydropyranyloxymethyl)phenylpyruvate 
• 177326-64-6 ethyl 4-(2-tetrahydropyranyloxy)methylindole-2-carboxylate 
• 177326-66-8 4-(2-tetrahydropyranyloxy)methylindole-2-carboxylic acid 
• 89929-99-7 6-nitro-2-(2-tetrahydropyranyloxy)methyltoluene 
• 177326-68-0 3-methyl-4-(2-tetrahydropyranyloxy)methylindole-2-carboxylic acid 

Relevant academic research and scientific papers

NosN, a Radical S-Adenosylmethionine Methylase, Catalyzes Both C1 Transfer and Formation of the Ester Linkage of the Side-Ring System during the Biosynthesis of Nosiheptide

Nosiheptide, a member of the e series of macrocyclic thiopeptide natural products, contains a side-ring system composed of a 3,4-dimethylindolic acid (DMIA) moiety connected to Glu6 and Cys8 of the thiopeptide backbone via ester and thioester linkages, re

Total Synthesis of Nosiheptide

Total synthesis of the bismacrocyclic thiopeptide antibiotic nosiheptide was achieved through the assembly of a fully functionalized linear precursor followed by consecutive macrocyclizations. Key features are a critical macrothiolactonization and a mild deprotection strategy for the 3-hydroxypyridine core. The natural product was identical to isolated authentic material in terms of spectral data and antibiotic activity.

Assembly of the nosiheptide A-ring: A fruitful lesson

The synthesis of a 28-membered thiopeptide macrocycle is described. Key steps are mild aza-Wittig thiazole ring closures, a scandium(III)-mediated regioselective ester hydrolysis, and a highly efficient macrolactam formation with its 3-hydroxypyridine nucleus orthogonally protected. Georg Thieme Verlag Stuttgart, New York.

Convenient synthesis of fragment E of antibiotic, nosiheptide

A convenient synthesis of Fragment E, 4-hydroxymethyl-3-methylindole-2-earboxylic acid (1), from 2-methyl-3-nitrobenzyl alcohol through six steps conversion in 32 % overall yield is described.