Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1)
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2013
Authors
Marjanovic, Jasna
Divjakovic, Vladimir
Matović, Radomir

Ferjančić, Zorana

Saičić, Radomir N.

Article (Published version)

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Show full item recordAbstract
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 reactionsSource:
European Journal of Organic Chemistry, 2013, 2013, 25, 5555-5560Publisher:
- 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
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IHTMTY - 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 . .