126522-30-3

Upstream product

• 123154-32-5 (Z),(S)-3-(3-methoxycarbonyl-1-butenyl)-1-tosylindole 
• 487-89-8 Indole-3-carboxaldehyde 
• 73295-10-0 (S)-3-acetoxy-2-methyl-propionic acid methyl ester 
• 98-59-9 p-toluenesulfonyl chloride 
• 123154-31-4 (R)-2-methoxycarbonylpropyltriphenylphosphonium bromide 
• 110556-33-7 (R)-3-bromo-2-methylpropionic acid methyl ester 
• 80657-57-4 3-hydroxy-(2S)-methylpropionate 
• 50562-79-3 1-(4-tolylsulfonyl)indole-3-carboxaldehyde 

Relevant academic research and scientific papers

SYNTHESIS OF THE (S)-ENANTIOMER OF PANICULIDINE A. ABSOLUTE CONFIGURATION OF NATURAL PANICULIDINES

The (S)-enantiomer of paniculidine A (an indole alkaloid from the plant Murraya paniculata) was synthesized from (R)-5-acetoxy-4-methylpentanoic acid by its oxidative transformation into (S)-methyl 2-methyl-3-acetoxypropionate, substitution of the acetoxy group by bromine, Wittig reaction of (R)-2-methoxycarbonylpropyltriphenylphosphonium bromide with 1-tosyl-3-formylindole, hydrogenation of the side chain of (Z,S)-3-(3-methoxycarbonyl-1-butenyl)-tosylindole and reductive desulfonylation of (S)-3-(3-methoxycarbonylbutyl)-1-tosylindole.Comparison of the D values of the synthesized (S)-paniculidine A with published data for the natural product showed that the latter has the (R) configuration.Condensation of the (R)-4-(2-tetrahydropyranyloxy)-3-methylbromobutane obtained from (R)-5-acetoxy-4-methylpentanoic acid with β-indolylmagnesium iodide followed by removal of the tetrahydropyranyl protecting group gave the (R)-enantiomer of paniculidinol .Its (S)-enantiomer was prepared by hydride reduction of (S)-paniculidine A.

Synthesis of the S-Enantiomer of Paniculidine A: Absolute R-Configuration of the Natural Paniculidines A and B

The absolute R-configuration of both the title monochiral indole alkaloids has been established.