ERC-project

Research funded by ERC-consolidator grant “BENOVELTY” (101000893)

In this project, we plan to develop novel saturated bioisosteres of benzenes:

ERC-topic

Publications on the ERC-project

13) 2-Oxabicyclo[2.1.1]hexanes: synthesis, properties and validation as bioisosteres of ortho- and meta-Benzenes
V. V. Levterov, Y. Panasiuk, O. Shablykin, O. Stashkevych, K. Sahun, A. Rassokhin, I. Sadkova, D. Lesyk, A. Anisiforova, Y. Holota, P. Borysko, I. Bodenchuk, N. M. Voloshchuk, P. K. Mykhailiuk*
Angew. Chem. Int. Ed. 2024, 63, e202319831
2-Oxabicyclo[2.1.1]hexanes: synthesis, properties and validation as bioisosteres of ortho- and meta-Benzenes

12) Spiro[3.3]heptane as a Saturated Benzene Bioisostere
K. Prysiazhniuk, O. P. Datsenko, O. Polishchuk, S. Shulha, O. Shablykin, Y. Nikandrova, K. Horbatok, I. Bodenchuk, P. Borysko, D. Shepilov, I. Pishel, V. Kubyshkin, P. K. Mykhailiuk*
Angew. Chem. Int. Ed. 2024, 63, e202316557
Spiro[3.3]heptane as a Saturated Benzene Bioisostere

11) Borylated cyclobutanes via thermal [2 + 2]-cycloaddition
K. Prysiazhniuk, O. Polishchuk, S. Shulha, K. Gudzikevych, O. P. Datsenko, V. Kubyshkin, P. K. Mykhailiuk*
Chem. Sci. 2024, 15, 3249-3254
Borylated cyclobutanes via thermal [2 + 2]-cycloaddition

10) 1-Azaspiro[3.3]heptane as a Bioisostere of Piperidine
A. A. Kirichok, H. Tkachuk, Y. Kozyriev, O. Shablykin, O. Datsenko, D. Granat, T. Yegorova, Y. P. Bas, V. Semirenko, I. Pishel, V. Kubyshkin, D. Lesyk, O. Klymenko-Ulianov, P. K. Mykhailiuk*
Angew. Chem. Int. Ed. 2023, 62, e202311583
1-Azaspiro[3.3]heptane as a Bioisostere of Piperidine

9) 1,2-Disubstituted bicyclo[2.1.1]hexanes as saturated bioisosteres of ortho-substituted benzene
V. A. Denisenko, P. Garbuz, Y. Makovetska, O. Shablykin, D. Lesyk, G. Al-Maali, R. Korzh, I. V. Sadkova, P. K. Mykhailiuk*
Chem. Sci. 2023, 14, 14092-14099
1,2-Disubstituted bicyclo[2.1.1]hexanes as saturated bioisosteres of ortho-substituted benzene

8) 2-Oxabicyclo[2.2.2]octane as a new bioisostere of the phenyl ring
V. V. Levterov, Y. Panasiuk, K. Sahun, O. Stashkevych, V. Badlo, O. Shablykin, I. Sadkova, L. Bortnichuk, O. Klymenko-Ulianov, Y. Holota, L. Lachmann, P. Borysko, K. Horbatok, I. Bodenchuk, Y. Bas, D. Dudenko, P. K. Mykhailiuk*
Nat. Commun. 2023, 14, 5608
2-Oxabicyclo[2.2.2]octane as a new bioisostere of the phenyl ring

7) 2-Oxabicyclo[2.1.1]hexanes as saturated bioisosteres of the ortho-substituted phenyl ring
A. Denisenko, P. Garbuz, N. M. Voloshchuk, Y. Holota, P. K. Mykhailiuk*
Nat. Chem. 2023, 15, 1155–1163
Water-soluble Bioisosteres of the ortho-substituted Phenyl Ring

6) General Synthesis of 3-Azabicyclo[3.1.1]heptanes and Evaluation of Their Properties as Saturated Bioisosteres
D. Dibchak, M. Snisarenko, A. Mishuk, O. Shablykin, L. Bortnichuk, O. Klymenko-Ulianov, Y. Kheylik, I. V. Sadkova, H. S. Rzepa, P. K. Mykhailiuk*
Angew. Chem. Int. Ed. 2023, 62, e202304246
General Synthesis of 3-Azabicyclo[3.1.1]heptanes and Evaluation of Their Properties as Saturated Bioisosteres

5) Rapid and scalable halosulfonylation of strain-release reagents
H. D. Pickford, V. Ripenko, R. E. McNamee, S. Holovchuk, A. L. Thompson, R. C. Smith, P. K. Mykhailiuk,* E. A. Anderson*
Angew. Chem. Int. Ed. 2023, 62, e202213508

Rapid and scalable halosulfonylation of strain-release reagents

 

4) A Practical and Scalable Approach to Fluoro-Substituted Bicyclo[1.1.1]pentanes
R. Bychek, P. K. Mykhailiuk*
Angew. Chem. Int. Ed. 2022, 61, e202205103
A Practical and Scalable Approach to Fluoro-Substituted Bicyclo[1.1.1]pentanes

3) Unexpected Isomerization of Oxetane-Carboxylic Acids
B. Chalyk, A. Grynyova, K. Filimonova, T. V. Rudenko, D. Dibchak, P. K. Mykhailiuk*
Org. Lett. 2022, 24, 4722-4728
Unexpected Isomerization of Oxetane-Carboxylic Acids

2) Oxa-spirocycles: synthesis, properties and applications
K. Fominova, T. Diachuk, D. Granat, T. Savchuk, V. Vilchynskyi, O. Svitlychnyi, V. Meliantsev, I. Kovalchuk, E. Litskan, V. V. Levterov, V. R. Badlo, R. I. Vaskevych, A. I. Vaskevych, A. V. Bolbut, V. V. Semeno, R. Iminov, K. Shvydenko, A. S. Kuznetsova, Y. V. Dmytriv, D. Vysochyn, V. Ripenko, A. A. Tolmachev, O. Pavlova, H. Kuznietsova, I. Pishel, P. Borysko, P. K. Mykhailiuk*
Chem. Sci. 2021, 12, 11294-11305
Oxa-spirocycles: synthesis, properties and applications

1) Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)
V. Ripenko, D. Vysochyn, I. Klymov, S. Zhersh, P. K. Mykhailiuk*
J. Org. Chem. 2021, 86, 14061-14068
Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)

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