Ripenko V. Synthesis and investigation of functionalized bicyclo[1.1.1]pentanes

Українська версія

Thesis for the degree of Doctor of Philosophy (PhD)

State registration number

0826U005107

Thesis Registration Form

0826U005107.pdf

Applicant for

Specialization

  • 102 - Хімія

10-09-2026

Specialized Academic Board

PhD 16791

Taras Shevchenko National University of Kyiv

Essay

This dissertation is devoted to the optimization and development of practical, scalable methods for the synthesis of functionalized bicyclo[1.1.1]pentanes (BCPs) — saturated bioisosteres of para-substituted benzene that have found widespread application in medicinal chemistry (over 2,300 BCP-containing patent applications indexed in CAS SciFinder as of 2026). Existing synthetic methods required mediumpressure mercury lamps with specialized glassware (Pyrex, quartz), expensive iridium photocatalysts, or pyrophoric initiators (Et₃B), precluding scale-up to industrially relevant quantities.

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Research papers

Ripenko V., Vysochyn D., Klymov I., Zhersh S., Mykhailiuk P. K. Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP). Journal of Organic Chemistry, 2021, 86, 14061–14068. DOI: 10.1021/acs.joc.1c00977.

Pickford H. D., Ripenko V., McNamee R. E., Holovchuk S., Thompson A. L., Smith R. C., Mykhailiuk P. K., Anderson E. A. Rapid and Scalable Halosulfonylation of Strain-Release Reagents. Angewandte Chemie International Edition, 2023, 62, e202213508. DOI: 10.1002/anie.202213508.

Ripenko V., Holovchuk S., Vysochyn D., Klymov I., Zhersh S., Mykhailiuk P. K. Light-Enabled Scalable Synthesis of Bicyclo[1.1.1]pentane Halides and Their Functionalizations. Nature Synthesis, 2024, 3, 1400–1410. DOI: 10.1038/s44160- 024-00637-y.

Ripenko V., Yegorova T. Synthesis of Functionalized Methyl-Substituted Bicyclo[1.1.1]pentanes. French-Ukrainian Journal of Chemistry, 2024, 12(1), 111–117. DOI: 10.17721/fujcV12I1P111-117.

Holota Y., Ripenko V., Lesyk A. et al. The activity of Benzocaine phenyl ring bioisosteres. SCF Chemical Biology Symposium 2024 «Chemistry meets Biology», January 24–26, 2024, P81.

Oleksiak O. M., Ripenko V. V., Kosach V. R. Multiplexed High Content Imaging assay optimization for the analysis of apoptosis/necrosis in breast cancer cells after treatment with Vorinostat analogues. BioGENext Conference: Shaping the future of medicine through biomedical R&D, September 17–20, 2024.

Ripenko V., Sham V., Levchenko V., Holovchuk S., Vysochyn D., Klymov I., Kyslyi D., Veselovych S., Zhersh S., Kolodiazhna O., Dmytriv Y., Tolmachev A., Sadkova I., Pishel I., Horbatok K., Kosach V., Nikandrova Y., Mykhailiuk P. K. Light-enabled scalable synthesis of bicyclo[1.1.1]pentane halides and their functionalizations. Frontiers in Medicinal Chemistry 2025, April 1–4, 2025, Erlangen, Germany (постерна доповідь, p. 62).

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Files

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