TY  - JOUR
AU  - Jovanović, Predrag
AU  - Petković, Miloš
AU  - Simić, Milena
AU  - Jovanović, Miloš
AU  - Tasić, Gordana
AU  - Crnogorac, Marija Dj.
AU  - Žižak, Željko
AU  - Savić, Vladimir
PY  - 2019
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5329
AB  - A novel synthetic route for highly substituted conjugated ketones has been developed utilizing glycals as starting materials. The two-step process combined the Heck reaction/Lewis acid promoted ring opening to afford the products in 33–80 % overall yields and with a high level of trans stereoselectivity. Since the products are essentially the aldols, this methodology may be employed in some cases as an alternative synthetic route to the typical aldol condensation. Densely substituted, selectively protected conjugated ketones are synthetically attractive structures which, in our case, proved to be biologically equally appealing. Namely, they showed activity against several cancer cell lines, such as HeLa, K562, MDA-MB-453, in some instances overperforming cisplatin used as a standard.
PB  - Wiley-VCH Verlag
T2  - European Journal of Organic Chemistry
T1  - Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals
VL  - 2019
IS  - 29
SP  - 4701
EP  - 4709
DO  - 10.1002/ejoc.201900672
ER  - 

@article{
author = "Jovanović, Predrag and Petković, Miloš and Simić, Milena and Jovanović, Miloš and Tasić, Gordana and Crnogorac, Marija Dj. and Žižak, Željko and Savić, Vladimir",
year = "2019",
abstract = "A novel synthetic route for highly substituted conjugated ketones has been developed utilizing glycals as starting materials. The two-step process combined the Heck reaction/Lewis acid promoted ring opening to afford the products in 33–80 % overall yields and with a high level of trans stereoselectivity. Since the products are essentially the aldols, this methodology may be employed in some cases as an alternative synthetic route to the typical aldol condensation. Densely substituted, selectively protected conjugated ketones are synthetically attractive structures which, in our case, proved to be biologically equally appealing. Namely, they showed activity against several cancer cell lines, such as HeLa, K562, MDA-MB-453, in some instances overperforming cisplatin used as a standard.",
publisher = "Wiley-VCH Verlag",
journal = "European Journal of Organic Chemistry",
title = "Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals",
volume = "2019",
number = "29",
pages = "4701-4709",
doi = "10.1002/ejoc.201900672"
}

Jovanović, P., Petković, M., Simić, M., Jovanović, M., Tasić, G., Crnogorac, M. Dj., Žižak, Ž.,& Savić, V.. (2019). Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals. in European Journal of Organic Chemistry
Wiley-VCH Verlag., 2019(29), 4701-4709.
https://doi.org/10.1002/ejoc.201900672

Jovanović P, Petković M, Simić M, Jovanović M, Tasić G, Crnogorac MD, Žižak Ž, Savić V. Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals. in European Journal of Organic Chemistry. 2019;2019(29):4701-4709.
doi:10.1002/ejoc.201900672 .

Jovanović, Predrag, Petković, Miloš, Simić, Milena, Jovanović, Miloš, Tasić, Gordana, Crnogorac, Marija Dj., Žižak, Željko, Savić, Vladimir, "Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals" in European Journal of Organic Chemistry, 2019, no. 29 (2019):4701-4709,
https://doi.org/10.1002/ejoc.201900672 . .