TY  - JOUR
AU  - Trmčić, Milena
AU  - Vulović, Bojan
AU  - Zlatar, Matija
AU  - Saičić, Radomir N.
PY  - 2024
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7041
AB  - Hemiacetals of cyclopropanone can be isolated and stocked, contrary to their highly reactive parent ketone.  However, they are not readily converted to cyclopropanone, which limits their use as its synthetic equivalents.  2,2,2-trifluoroethoxy hemiacetals are expected to be better cyclopropanone surrogates, however, they have  never been prepared, so far. We show that oxyallyl cations with a heteroatom in the -position can be  intercepted with 2,2,2-trifluoroethanol, with formation of cyclopropanone trifluoroethoxy hemiacetals stable  enough to be isolated, purified and characterized. These species can serve as synthetic equivalents of  cyclopropanone under mild conditions.
PB  - ARKAT USA, Inc.
T2  - ARKIVOC - Online Journal of Organic Chemistry
T1  - Preparation of cyclopropanone 2,2,2-trifluoroethoxy hemiacetals via oxyallyl cation
VL  - 2024
IS  - 2
DO  - 10.24820/ark.5550190.p012.123
ER  - 

@article{
author = "Trmčić, Milena and Vulović, Bojan and Zlatar, Matija and Saičić, Radomir N.",
year = "2024",
abstract = "Hemiacetals of cyclopropanone can be isolated and stocked, contrary to their highly reactive parent ketone.  However, they are not readily converted to cyclopropanone, which limits their use as its synthetic equivalents.  2,2,2-trifluoroethoxy hemiacetals are expected to be better cyclopropanone surrogates, however, they have  never been prepared, so far. We show that oxyallyl cations with a heteroatom in the -position can be  intercepted with 2,2,2-trifluoroethanol, with formation of cyclopropanone trifluoroethoxy hemiacetals stable  enough to be isolated, purified and characterized. These species can serve as synthetic equivalents of  cyclopropanone under mild conditions.",
publisher = "ARKAT USA, Inc.",
journal = "ARKIVOC - Online Journal of Organic Chemistry",
title = "Preparation of cyclopropanone 2,2,2-trifluoroethoxy hemiacetals via oxyallyl cation",
volume = "2024",
number = "2",
doi = "10.24820/ark.5550190.p012.123"
}

Trmčić, M., Vulović, B., Zlatar, M.,& Saičić, R. N.. (2024). Preparation of cyclopropanone 2,2,2-trifluoroethoxy hemiacetals via oxyallyl cation. in ARKIVOC - Online Journal of Organic Chemistry
ARKAT USA, Inc.., 2024(2).
https://doi.org/10.24820/ark.5550190.p012.123

Trmčić M, Vulović B, Zlatar M, Saičić RN. Preparation of cyclopropanone 2,2,2-trifluoroethoxy hemiacetals via oxyallyl cation. in ARKIVOC - Online Journal of Organic Chemistry. 2024;2024(2).
doi:10.24820/ark.5550190.p012.123 .

Trmčić, Milena, Vulović, Bojan, Zlatar, Matija, Saičić, Radomir N., "Preparation of cyclopropanone 2,2,2-trifluoroethoxy hemiacetals via oxyallyl cation" in ARKIVOC - Online Journal of Organic Chemistry, 2024, no. 2 (2024),
https://doi.org/10.24820/ark.5550190.p012.123 . .

TY  - JOUR
AU  - Vulović, Bojan
AU  - Trmčić, Milena
AU  - Matović, Radomir
AU  - Saičić, Radomir N.
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3819
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3388
AB  - Unsaturated oxyallyl cations with a suitably positioned alkene bond undergo 5-exo-cyclization with the formation of vinylcyclopentane derivatives. Alkyne analogues provide allenes. The reaction proceeds with a moderate to excellent level of stereoselectivity and allows for asymmetric induction in the reaction with chiral substrate.
PB  - American Chemical Society (ACS)
T2  - Organic Letters
T1  - Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation
VL  - 21
IS  - 23
SP  - 9618
EP  - 9621
DO  - 10.1021/acs.orglett.9b03791
ER  - 

@article{
author = "Vulović, Bojan and Trmčić, Milena and Matović, Radomir and Saičić, Radomir N.",
year = "2019",
abstract = "Unsaturated oxyallyl cations with a suitably positioned alkene bond undergo 5-exo-cyclization with the formation of vinylcyclopentane derivatives. Alkyne analogues provide allenes. The reaction proceeds with a moderate to excellent level of stereoselectivity and allows for asymmetric induction in the reaction with chiral substrate.",
publisher = "American Chemical Society (ACS)",
journal = "Organic Letters",
title = "Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation",
volume = "21",
number = "23",
pages = "9618-9621",
doi = "10.1021/acs.orglett.9b03791"
}

Vulović, B., Trmčić, M., Matović, R.,& Saičić, R. N.. (2019). Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation. in Organic Letters
American Chemical Society (ACS)., 21(23), 9618-9621.
https://doi.org/10.1021/acs.orglett.9b03791

Vulović B, Trmčić M, Matović R, Saičić RN. Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation. in Organic Letters. 2019;21(23):9618-9621.
doi:10.1021/acs.orglett.9b03791 .

Vulović, Bojan, Trmčić, Milena, Matović, Radomir, Saičić, Radomir N., "Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation" in Organic Letters, 21, no. 23 (2019):9618-9621,
https://doi.org/10.1021/acs.orglett.9b03791 . .

TY  - JOUR
AU  - Novkovic, L
AU  - Trmcic, M
AU  - Rodić, Marko V.
AU  - Bihelović, Filip
AU  - Zlatar, Matija
AU  - Matović, Radomir
AU  - Saičić, Radomir N.
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1796
AB  - Domino reactions of ketones with molecular oxygen in the presence of potassium hydroxide and potassium t-butoxide afford cyclic hydroperoxy acetals (3,5-dihydroxy-1,2-dioxanes). Mixed endoperoxides can also be obtained in a three-component reaction of two ketones and oxygen.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen
VL  - 5
IS  - 120
SP  - 99577
EP  - 99584
DO  - 10.1039/c5ra13476e
ER  - 

@article{
author = "Novkovic, L and Trmcic, M and Rodić, Marko V. and Bihelović, Filip and Zlatar, Matija and Matović, Radomir and Saičić, Radomir N.",
year = "2015",
abstract = "Domino reactions of ketones with molecular oxygen in the presence of potassium hydroxide and potassium t-butoxide afford cyclic hydroperoxy acetals (3,5-dihydroxy-1,2-dioxanes). Mixed endoperoxides can also be obtained in a three-component reaction of two ketones and oxygen.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen",
volume = "5",
number = "120",
pages = "99577-99584",
doi = "10.1039/c5ra13476e"
}

Novkovic, L., Trmcic, M., Rodić, M. V., Bihelović, F., Zlatar, M., Matović, R.,& Saičić, R. N.. (2015). Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen. in RSC Advances
Royal Soc Chemistry, Cambridge., 5(120), 99577-99584.
https://doi.org/10.1039/c5ra13476e

Novkovic L, Trmcic M, Rodić MV, Bihelović F, Zlatar M, Matović R, Saičić RN. Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen. in RSC Advances. 2015;5(120):99577-99584.
doi:10.1039/c5ra13476e .

Novkovic, L, Trmcic, M, Rodić, Marko V., Bihelović, Filip, Zlatar, Matija, Matović, Radomir, Saičić, Radomir N., "Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen" in RSC Advances, 5, no. 120 (2015):99577-99584,
https://doi.org/10.1039/c5ra13476e . .

TY  - JOUR
AU  - Trmcic, Milena V.
AU  - Matović, Radomir
AU  - Tovilović, Gordana
AU  - Ristic, Biljana Z.
AU  - Trajković, Vladimir
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir N.
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/981
AB  - The design, synthesis and biological evaluation of a novel C, D-spirolactone analogue of paclitaxel is described. This is the first paclitaxel analogue without an oxetane D-ring that shows a significant cytotoxic effect (activity one order of magnitude lower than paclitaxel). More importantly, its cytotoxicity is a result of a different mechanism of action, involving mTOR inhibition-dependent autophagy instead of G(2)/M cell cycle arrest-dependent apoptosis.
PB  - Royal Soc Chemistry, Cambridge
T2  - Organic & Biomolecular Chemistry
T1  - A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids
VL  - 10
IS  - 25
SP  - 4933
EP  - 4942
DO  - 10.1039/c2ob25514f
ER  - 

@article{
author = "Trmcic, Milena V. and Matović, Radomir and Tovilović, Gordana and Ristic, Biljana Z. and Trajković, Vladimir and Ferjančić, Zorana and Saičić, Radomir N.",
year = "2012",
abstract = "The design, synthesis and biological evaluation of a novel C, D-spirolactone analogue of paclitaxel is described. This is the first paclitaxel analogue without an oxetane D-ring that shows a significant cytotoxic effect (activity one order of magnitude lower than paclitaxel). More importantly, its cytotoxicity is a result of a different mechanism of action, involving mTOR inhibition-dependent autophagy instead of G(2)/M cell cycle arrest-dependent apoptosis.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Organic & Biomolecular Chemistry",
title = "A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids",
volume = "10",
number = "25",
pages = "4933-4942",
doi = "10.1039/c2ob25514f"
}

Trmcic, M. V., Matović, R., Tovilović, G., Ristic, B. Z., Trajković, V., Ferjančić, Z.,& Saičić, R. N.. (2012). A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids. in Organic & Biomolecular Chemistry
Royal Soc Chemistry, Cambridge., 10(25), 4933-4942.
https://doi.org/10.1039/c2ob25514f

Trmcic MV, Matović R, Tovilović G, Ristic BZ, Trajković V, Ferjančić Z, Saičić RN. A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids. in Organic & Biomolecular Chemistry. 2012;10(25):4933-4942.
doi:10.1039/c2ob25514f .

Trmcic, Milena V., Matović, Radomir, Tovilović, Gordana, Ristic, Biljana Z., Trajković, Vladimir, Ferjančić, Zorana, Saičić, Radomir N., "A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids" in Organic & Biomolecular Chemistry, 10, no. 25 (2012):4933-4942,
https://doi.org/10.1039/c2ob25514f . .