123154-31-4Relevant academic research and scientific papers
SYNTHESIS OF THE (S)-ENANTIOMER OF PANICULIDINE A. ABSOLUTE CONFIGURATION OF NATURAL PANICULIDINES
Cheskis, B. A.,Alekseev, I. G.,Moiseenkov, A. M.
, p. 364 - 369 (2007/10/02)
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
Czeskis, Boris A.,Moissenkov, Alexander M.
, p. 1353 - 1354 (2007/10/02)
The absolute R-configuration of both the title monochiral indole alkaloids has been established.
