404888-90-0

Upstream product

• 4248-19-5 tert-butyl carbazate 
• 354538-27-5 6-bromo-1-tosyl-3-vinyl-1H-indole 
• 404888-85-3 (R)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(tosyl)oxy]-1-ethanol 
• 404888-89-7 (R)-1-(N-tosyl-6-bromoindol-3-yl)-2-azido-1-ethanol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 404888-82-0 (R)-1-(N-tosyl-6-bromoindol-3-yl)-1,2-ethanediol 

Downstream Products

• 404888-95-5 (S)-N-[2-azido-2-(N-tosyl-6-bromo-indol-3-yl)ethyl]-2-(6-bromo-1H-indol-3-yl)-2-oxoacetamide 
• 404888-96-6 (S)-3-(6-bromoindol-3-yl)-5-(N-tosyl-6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone 
• 404888-93-3 (S)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-1-azidoethylamine 

Relevant academic research and scientific papers

Enantioseleetive synthesis of marine indole alkaloid hamacanthin B

An enantioselective total synthesis of hamacanthin B (1) is described. This synthesis is based on the asymmetric synthesis of (S)-2-azido-(indol-3-yl)ethylamine 7, which is coupled with the 3-indolyl-α-oxoacetyl chloride 8 and subsequently used in a successful intramolecular Staudinger-aza Wittig cyclization to form the central dihydropyrazinone ring. The stereochemistry of naturally isolated hamacanthin B is revealed as the (S)-configuration.

Asymmetric aminohydroxylation of vinyl indoles: A short enantioselective synthesis of the bisindole alkaloids dihydrohamacanthin A and dragmacidin A

A useful approach for the direct enantioselective synthesis of (S)-N-Boc-protected α-indol-3-ylglycinols from vinyl indoles using the Sharpless asymmetric aminohydroxylation reaction, with enantioselectivities of up to 94% and isolated yields of up to 65%