1173180-39-6

Basic information

• Product Name: chaetominine
• CAS NO: 1173180-39-6
• Molecular Weight: 402.409
• Mol File: 1173180-39-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: chaetominine(CAS DataBase Reference)
• NIST Chemistry Reference: chaetominine(1173180-39-6)
• EPA Substance Registry System: chaetominine(1173180-39-6)

Safety Data

• Hazardous Substances Data: 1173180-39-6(Hazardous Substances Data)

Upstream product

• 27261-93-4 (S)-3-(1H-indol-3-yl)-2-(2-nitrobenzamido)propanoic acid 
• 552-16-9 ortho-nitrobenzoic acid 
• 610-14-0 2-nitrobenzyl chloride 
• 1602783-25-4 methyl (S)-{2-[(S)-3-(1H-indol-3-yl)-2-(2-nitrobenzamido)propanamido]propanoate} 
• 1602783-27-6 (S)-2-[(S)-3-(1H-indol-3-yl)-2-(4-oxo-4H-quinazolin-3-yl)propionylamino]propionic acid methyl ester 
• 1190111-93-3 (R)-3-(1H-indol-3-yl)-2-(4-oxo-4H-quinazolin-3-yl)-propionic acid methyl ester 
• 1173180-37-4 (S)-2-[(R)-3-(1H-indol-3-yl)-2-(4-oxo-4H-quinazolin-3-yl)-proprionylamino]propionic acid methyl ester 
• 14907-27-8 (R)-(+)-tryptophan methyl ester hydrochloride 
• 118-48-9 isatoic anhydride 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 205042-94-0 N-(2-aminobenzoyl)-D-tryptophan methyl ester 
• 1190112-03-8 C₁₉H₁₅N₃O₃ 
• 85612-29-9 N_b-(2-aminobenzoyl)-L-tryptophan methyl ester 
• 72144-94-6 3-indol-3-yl-2-(4-oxo-4H-quinazolin-3-yl)-propionic acid 

Relevant articles and documents

Complexity generation by chemical synthesis: A five-step synthesis of (-)-chaetominine from l-tryptophan and its biosynthetic implications

We demonstrated, for the first time, that on the basis of chemistry principles, the hexacyclic peptidyl alkaloid (-)-chaetominine (1) can be synthesized in a straightforward manner from l-Trp. The approach features the efficient generation of molecular complexity via a tandem C3/C14 syn-selective epoxidation (dr = 3:2)-annulative ring-opening reaction and a regioselective epimerization at C14. The successful production of (-)-chaetominine (1) from l-Trp could be helpful for revealing how the configuration of l-tryptophan becomes inverted in the biosynthetic pathway of (-)-chaetominine (1). This journal is the Partner Organisations 2014.

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