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Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence
A tactical combination of either (S)- or (R)-proline catalyzed aldol reaction followed by intramolecular reductive amination enabled the synthesis of a chiral pyrrolidine derivative with 3 contiguous stereocenters in only 2 synthetic steps, starting from achiral precursors. This product, obtainable in both enantiomeric forms, was further exploited as a common intermediate in total syntheses of the biologically active iminosugars: ( + )-swainsonine, (–)-swainsonine, ( + )-8-epi-swainsonine, and ( + )-dideoxy-imino-lyxitol.
TY - JOUR
AU - Trajković, Miloš D.
AU - Pavlović, Miloš
AU - Bihelović, Filip
AU - Ferjančić, Zorana
AU - Saičić, Radomir
PY - 2022
UR - https://doi.org/10.1177/1934578X221091672
UR - http://cherry.chem.bg.ac.rs/handle/123456789/5179
AB - A tactical combination of either (S)- or (R)-proline catalyzed aldol reaction followed by intramolecular reductive amination enabled the synthesis of a chiral pyrrolidine derivative with 3 contiguous stereocenters in only 2 synthetic steps, starting from achiral precursors. This product, obtainable in both enantiomeric forms, was further exploited as a common intermediate in total syntheses of the biologically active iminosugars: ( + )-swainsonine, (–)-swainsonine, ( + )-8-epi-swainsonine, and ( + )-dideoxy-imino-lyxitol.
PB - SAGE Publications
T2 - Natural Product Communications
T2 - Natural Product CommunicationsNatural Product Communications
T1 - Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence
VL - 17
IS - 4
DO - 10.1177/1934578X221091672
ER -
@article{
author = "Trajković, Miloš D. and Pavlović, Miloš and Bihelović, Filip and Ferjančić, Zorana and Saičić, Radomir",
year = "2022",
abstract = "A tactical combination of either (S)- or (R)-proline catalyzed aldol reaction followed by intramolecular reductive amination enabled the synthesis of a chiral pyrrolidine derivative with 3 contiguous stereocenters in only 2 synthetic steps, starting from achiral precursors. This product, obtainable in both enantiomeric forms, was further exploited as a common intermediate in total syntheses of the biologically active iminosugars: ( + )-swainsonine, (–)-swainsonine, ( + )-8-epi-swainsonine, and ( + )-dideoxy-imino-lyxitol.",
publisher = "SAGE Publications",
journal = "Natural Product Communications, Natural Product CommunicationsNatural Product Communications",
title = "Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence",
volume = "17",
number = "4",
doi = "10.1177/1934578X221091672"
}
Trajković, M. D., Pavlović, M., Bihelović, F., Ferjančić, Z.,& Saičić, R.. (2022). Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence. in Natural Product Communications
SAGE Publications., 17(4).
https://doi.org/10.1177/1934578X221091672
Trajković MD, Pavlović M, Bihelović F, Ferjančić Z, Saičić R. Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence. in Natural Product Communications. 2022;17(4).
doi:10.1177/1934578X221091672 .
Trajković, Miloš D., Pavlović, Miloš, Bihelović, Filip, Ferjančić, Zorana, Saičić, Radomir, "Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence" in Natural Product Communications, 17, no. 4 (2022),
https://doi.org/10.1177/1934578X221091672 . .
