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Total synthesis and biological evaluation of (-)-atrop-abyssomicin C

Authorized Users Only
2013
Authors
Bihelović, Filip
Karadžić, Ivanka
Matović, Radomir
Saičić, Radomir N.
Article (Published version)
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Abstract
Enantioselective synthesis of a marine antibiotic (-)-atrop-abyssomicin C was accomplished in 21 steps, in 1.8% overall yield (4%, based on the recovered starting material). The key steps of the synthesis are the formation of the functionalized cyclohexane core by an organocatalyzed Tsuji-Trost reaction, the formation of a tricyclic spirotetronate unit by a gold-catalyzed reaction sequence and the highly efficient eleven-membered ring closure by a Nozaki-Hiyama-Kishi reaction. Biological tests showed all abyssomicin derivatives to possess strong antibacterial activity against methicillin resistant S. aureus strains; however, they also proved to be cytotoxic, both to malignant and to normal somatic cells.
Source:
Organic & Biomolecular Chemistry, 2013, 11, 33, 5413-5424
Publisher:
  • Royal Soc Chemistry, Cambridge
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)

DOI: 10.1039/c3ob40692j

ISSN: 1477-0520

PubMed: 23839049

WoS: 000323141800005

Scopus: 2-s2.0-84881172859
[ Google Scholar ]
27
26
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/1214
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Bihelović, Filip
AU  - Karadžić, Ivanka
AU  - Matović, Radomir
AU  - Saičić, Radomir N.
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1214
AB  - Enantioselective synthesis of a marine antibiotic (-)-atrop-abyssomicin C was accomplished in 21 steps, in 1.8% overall yield (4%, based on the recovered starting material). The key steps of the synthesis are the formation of the functionalized cyclohexane core by an organocatalyzed Tsuji-Trost reaction, the formation of a tricyclic spirotetronate unit by a gold-catalyzed reaction sequence and the highly efficient eleven-membered ring closure by a Nozaki-Hiyama-Kishi reaction. Biological tests showed all abyssomicin derivatives to possess strong antibacterial activity against methicillin resistant S. aureus strains; however, they also proved to be cytotoxic, both to malignant and to normal somatic cells.
PB  - Royal Soc Chemistry, Cambridge
T2  - Organic & Biomolecular Chemistry
T1  - Total synthesis and biological evaluation of (-)-atrop-abyssomicin C
VL  - 11
IS  - 33
SP  - 5413
EP  - 5424
DO  - 10.1039/c3ob40692j
ER  - 
@article{
author = "Bihelović, Filip and Karadžić, Ivanka and Matović, Radomir and Saičić, Radomir N.",
year = "2013",
abstract = "Enantioselective synthesis of a marine antibiotic (-)-atrop-abyssomicin C was accomplished in 21 steps, in 1.8% overall yield (4%, based on the recovered starting material). The key steps of the synthesis are the formation of the functionalized cyclohexane core by an organocatalyzed Tsuji-Trost reaction, the formation of a tricyclic spirotetronate unit by a gold-catalyzed reaction sequence and the highly efficient eleven-membered ring closure by a Nozaki-Hiyama-Kishi reaction. Biological tests showed all abyssomicin derivatives to possess strong antibacterial activity against methicillin resistant S. aureus strains; however, they also proved to be cytotoxic, both to malignant and to normal somatic cells.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Organic & Biomolecular Chemistry",
title = "Total synthesis and biological evaluation of (-)-atrop-abyssomicin C",
volume = "11",
number = "33",
pages = "5413-5424",
doi = "10.1039/c3ob40692j"
}
Bihelović, F., Karadžić, I., Matović, R.,& Saičić, R. N.. (2013). Total synthesis and biological evaluation of (-)-atrop-abyssomicin C. in Organic & Biomolecular Chemistry
Royal Soc Chemistry, Cambridge., 11(33), 5413-5424.
https://doi.org/10.1039/c3ob40692j
Bihelović F, Karadžić I, Matović R, Saičić RN. Total synthesis and biological evaluation of (-)-atrop-abyssomicin C. in Organic & Biomolecular Chemistry. 2013;11(33):5413-5424.
doi:10.1039/c3ob40692j .
Bihelović, Filip, Karadžić, Ivanka, Matović, Radomir, Saičić, Radomir N., "Total synthesis and biological evaluation of (-)-atrop-abyssomicin C" in Organic & Biomolecular Chemistry, 11, no. 33 (2013):5413-5424,
https://doi.org/10.1039/c3ob40692j . .

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