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Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1)

Authorized Users Only
2013
Authors
Marjanovic, Jasna
Divjakovic, Vladimir
Matović, Radomir
Ferjančić, Zorana
Saičić, Radomir N.
Article (Published version)
Metadata
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Abstract
The stereodivergent synthesis of two hyacinthacine analogues, which relies on an organocatalyzed aldol addition, is described. The aldol addition of dioxanone to an -N-carbobenzyloxy-substituted chiral aldehyde, promoted by both (R)- and (S)-proline, proceeds in reasonable yields with acceptable diastereomeric ratios. The success of the reaction may be due to the use of an acyclic aldehyde acceptor, which allows reagent control of the stereochemical outcome of the key aldolization step in both the matched and mismatched cases.
Keywords:
Asymmetric synthesis / Azasugars / Natural products / Organocatalysis / Aldol reactions
Source:
European Journal of Organic Chemistry, 2013, 2013, 25, 5555-5560
Publisher:
  • Wiley-V C H Verlag Gmbh, Weinheim
Funding / projects:
  • The development of new synthetic methods and their application in the synthesis of natural products and biologically active molecules (RS-172027)
  • Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-256716)
  • Municipality of Stari Grad

DOI: 10.1002/ejoc.201300716

ISSN: 1434-193X

WoS: 000323319500004

Scopus: 2-s2.0-84882875459
[ Google Scholar ]
21
18
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/1215
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Marjanovic, Jasna
AU  - Divjakovic, Vladimir
AU  - Matović, Radomir
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir N.
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1215
AB  - The stereodivergent synthesis of two hyacinthacine analogues, which relies on an organocatalyzed aldol addition, is described. The aldol addition of dioxanone to an -N-carbobenzyloxy-substituted chiral aldehyde, promoted by both (R)- and (S)-proline, proceeds in reasonable yields with acceptable diastereomeric ratios. The success of the reaction may be due to the use of an acyclic aldehyde acceptor, which allows reagent control of the stereochemical outcome of the key aldolization step in both the matched and mismatched cases.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1)
VL  - 2013
IS  - 25
SP  - 5555
EP  - 5560
DO  - 10.1002/ejoc.201300716
ER  - 
@article{
author = "Marjanovic, Jasna and Divjakovic, Vladimir and Matović, Radomir and Ferjančić, Zorana and Saičić, Radomir N.",
year = "2013",
abstract = "The stereodivergent synthesis of two hyacinthacine analogues, which relies on an organocatalyzed aldol addition, is described. The aldol addition of dioxanone to an -N-carbobenzyloxy-substituted chiral aldehyde, promoted by both (R)- and (S)-proline, proceeds in reasonable yields with acceptable diastereomeric ratios. The success of the reaction may be due to the use of an acyclic aldehyde acceptor, which allows reagent control of the stereochemical outcome of the key aldolization step in both the matched and mismatched cases.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1)",
volume = "2013",
number = "25",
pages = "5555-5560",
doi = "10.1002/ejoc.201300716"
}
Marjanovic, J., Divjakovic, V., Matović, R., Ferjančić, Z.,& Saičić, R. N.. (2013). Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1). in European Journal of Organic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim., 2013(25), 5555-5560.
https://doi.org/10.1002/ejoc.201300716
Marjanovic J, Divjakovic V, Matović R, Ferjančić Z, Saičić RN. Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1). in European Journal of Organic Chemistry. 2013;2013(25):5555-5560.
doi:10.1002/ejoc.201300716 .
Marjanovic, Jasna, Divjakovic, Vladimir, Matović, Radomir, Ferjančić, Zorana, Saičić, Radomir N., "Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1)" in European Journal of Organic Chemistry, 2013, no. 25 (2013):5555-5560,
https://doi.org/10.1002/ejoc.201300716 . .

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