1465030-33-4

Upstream product

• 64951-03-7 methyl 2-(3-formyl-1H-indol-2-yl)acetate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 68-12-2 N,N-dimethyl-formamide 
• 5344-90-1 2-Aminobenzyl alcohol 
• 78133-84-3 (2-aminobenzyl)triphenylphosphonium bromide 
• 21422-40-2 methyl 1H-indole-2-acetate 
• 1508270-94-7 tert-butyl 2-(2-methoxy-2-oxoethyl)-1H-indole-1-carboxylate 

Downstream Products

• 1465031-27-9 (E)-1-(tert-butoxycarbonyl)-2-(1-(4-((tert-butoxycarbonyl)oxy)phenyl)-3-methoxy-3-oxoprop-1-en-2-yl)-1H-indole-3-carboxylic acid 
• 1465030-90-3 1-methoxycarbonyl-2-(4-hydroxyphenyl)-3-nitro-9H-carbazole 

Relevant academic research and scientific papers

A formal approach to the cyanobacterial sunscreen indole, prenostodione

The synthesis of the indole sunscreen pigment prenostodione was attempted via an LDA-initiated condensation of N-carbamate indole-2-methyl ester 22 with 4-[(t-butyldimethylsilyl)oxy]benzaldehyde (14) and a late-stage Vilsmeier-Haack formylation. Difficulties with the ensuing oxidation required installation of a C-3 carboxylic acid necessitating the use of a recently reported protocol and thus a formal synthesis of the natural product was realized from 2-aminobenzyl alcohol (17) in nine steps.

L-Proline catalyzed stereoselective synthesis of (E)-methyl-α-indol- 2-yl-β-aryl/alkyl acrylates: Easy access to substituted carbazoles, γ-carbolines and prenostodione

A simple, mild and robust method for the stereoselective synthesis of (E)-methyl α-(3-formyl-1H-indol-2-yl)-β-aryl/alkyl-substituted acrylates via a condensation reaction of methyl 2-(3-formyl-1H-indol-2-yl) acetate with several alkyl or aryl aldehydes using l-proline (25 mol%) as a catalyst is presented for the first time. In addition, completely metal free based high yielding methods for the syntheses of highly substituted biologically important carbazoles, γ-carbolines and the marine alkaloid prenostodione have been developed through our methodology.