Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)

[Image: see text] In flow photochemical addition of propellane to diacetyl allowed construction of the bicyclo[1.1.1]pentane (BCP) core in a 1 kg scale within 1 day. Haloform reaction of the formed diketone in batch afforded bicyclo[1.1.1]pentane-1,3-dicarboxylic acid in a multigram amount. Represen...

Descripción completa

Detalles Bibliográficos
Autores principales: Ripenko, Vasyl, Vysochyn, Daniil, Klymov, Ivan, Zhersh, Serhii, Mykhailiuk, Pavel K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8524415/
https://www.ncbi.nlm.nih.gov/pubmed/34166594
http://dx.doi.org/10.1021/acs.joc.1c00977
_version_ 1784585507770990592
author Ripenko, Vasyl
Vysochyn, Daniil
Klymov, Ivan
Zhersh, Serhii
Mykhailiuk, Pavel K.
author_facet Ripenko, Vasyl
Vysochyn, Daniil
Klymov, Ivan
Zhersh, Serhii
Mykhailiuk, Pavel K.
author_sort Ripenko, Vasyl
collection PubMed
description [Image: see text] In flow photochemical addition of propellane to diacetyl allowed construction of the bicyclo[1.1.1]pentane (BCP) core in a 1 kg scale within 1 day. Haloform reaction of the formed diketone in batch afforded bicyclo[1.1.1]pentane-1,3-dicarboxylic acid in a multigram amount. Representative gram scale transformations of the diacid were also performed to obtain various BCP-containing building blocks—alcohols, acids, amines, trifluoroborates, amino acids, etc.—for medicinal chemistry.
format Online
Article
Text
id pubmed-8524415
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-85244152021-10-19 Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP) Ripenko, Vasyl Vysochyn, Daniil Klymov, Ivan Zhersh, Serhii Mykhailiuk, Pavel K. J Org Chem [Image: see text] In flow photochemical addition of propellane to diacetyl allowed construction of the bicyclo[1.1.1]pentane (BCP) core in a 1 kg scale within 1 day. Haloform reaction of the formed diketone in batch afforded bicyclo[1.1.1]pentane-1,3-dicarboxylic acid in a multigram amount. Representative gram scale transformations of the diacid were also performed to obtain various BCP-containing building blocks—alcohols, acids, amines, trifluoroborates, amino acids, etc.—for medicinal chemistry. American Chemical Society 2021-06-24 2021-10-15 /pmc/articles/PMC8524415/ /pubmed/34166594 http://dx.doi.org/10.1021/acs.joc.1c00977 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Ripenko, Vasyl
Vysochyn, Daniil
Klymov, Ivan
Zhersh, Serhii
Mykhailiuk, Pavel K.
Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)
title Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)
title_full Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)
title_fullStr Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)
title_full_unstemmed Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)
title_short Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)
title_sort large-scale synthesis and modifications of bicyclo[1.1.1]pentane-1,3-dicarboxylic acid (bcp)
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8524415/
https://www.ncbi.nlm.nih.gov/pubmed/34166594
http://dx.doi.org/10.1021/acs.joc.1c00977
work_keys_str_mv AT ripenkovasyl largescalesynthesisandmodificationsofbicyclo111pentane13dicarboxylicacidbcp
AT vysochyndaniil largescalesynthesisandmodificationsofbicyclo111pentane13dicarboxylicacidbcp
AT klymovivan largescalesynthesisandmodificationsofbicyclo111pentane13dicarboxylicacidbcp
AT zhershserhii largescalesynthesisandmodificationsofbicyclo111pentane13dicarboxylicacidbcp
AT mykhailiukpavelk largescalesynthesisandmodificationsofbicyclo111pentane13dicarboxylicacidbcp

Ejemplares similares