1173180-35-2

Basic information

• Product Name: (R)-3-(1H-indol-3-yl)-2-(2-nitrobenzamido)propanoic acid
• Synonyms: (R)-3-(1H-indol-3-yl)-2-(2-nitrobenzamido)propanoic acid
• CAS NO: 1173180-35-2
• Molecular Weight: 353.334
• Mol File: 1173180-35-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (R)-3-(1H-indol-3-yl)-2-(2-nitrobenzamido)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(1H-indol-3-yl)-2-(2-nitrobenzamido)propanoic acid(1173180-35-2)
• EPA Substance Registry System: (R)-3-(1H-indol-3-yl)-2-(2-nitrobenzamido)propanoic acid(1173180-35-2)

Safety Data

• Hazardous Substances Data: 1173180-35-2(Hazardous Substances Data)

Upstream product

• 552-16-9 ortho-nitrobenzoic acid 
• 610-14-0 2-nitrobenzyl chloride 
• 153-94-6 D-tryptophan 

Downstream Products

• 918659-56-0 chaetominine 
• 1173180-36-3 methyl (S)-{2-[(R)-3-(1H-indol-3-yl)-2-(2-nitrobenzamido)propanamido]propanoate} 

Relevant articles and documents

Concise, enantioselective total syntheses of both the proposed and revised structures of (?)-versiquinazoline H

The enantioselective total synthesis of the putative structure of versiquinazoline H and three diastereomers has been achieved, which allowed the revision of the stereochemistry of this natural product. This six-step total synthesis relied on the evolution of the strategy that we previously developed, which features a DMDO-triggered tandem reaction. The modification of the lactamization step resulted in a significant improvement of yield that ensured the efficient total synthesis.

Bio-inspired step-economical, redox-economical and protecting-group-free enantioselective total syntheses of (-)-chaetominine and analogues

Full details of the enantioselective four-step and five-step total syntheses of (-)-chaetominine from D-Trp and L-Trp are described. Featuring an oxidative double cyclization reaction, and tandem C14 epimerization- lactamization reactions as key steps, the method provides a rapid access to (-)-chaetominine (6a) and analogues. The total syntheses of (-)-chaetominine (6a) are so far the most concise and efficient. Through comprehensive investigation, the stereochemical requirements for the double cyclization reaction were revealed, and the confusion regarding physicochemical properties of this natural product was clarified. Moreover, short pathways to complexity generation, a scenarios revealed for the biosynthesis of fungal peptidyl alkaloid multi-cyclic scaffolds, have been validated through the chemical synthesis. On the basis of these findings, a plausible biosynthetic pathway for (-)-chaetominine (6a) was suggested. Copyright