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.
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 . .
