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Conquering the Synthesis and Functionalization of Bicyclo[1.1.1]pentanes

[Image: see text] Bicyclo[1.1.1]pentanes (BCPs) have become established as attractive bioisosteres for para-substituted benzene rings in drug design. Conferring various beneficial properties compared with their aromatic “parents,” BCPs featuring a wide array of bridgehead substituents can now be acc...

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Autores principales: Shire, Bethany R., Anderson, Edward A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10301682/
https://www.ncbi.nlm.nih.gov/pubmed/37388694
http://dx.doi.org/10.1021/jacsau.3c00014
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author Shire, Bethany R.
Anderson, Edward A.
author_facet Shire, Bethany R.
Anderson, Edward A.
author_sort Shire, Bethany R.
collection PubMed
description [Image: see text] Bicyclo[1.1.1]pentanes (BCPs) have become established as attractive bioisosteres for para-substituted benzene rings in drug design. Conferring various beneficial properties compared with their aromatic “parents,” BCPs featuring a wide array of bridgehead substituents can now be accessed by an equivalent variety of methods. In this perspective, we discuss the evolution of this field and focus on the most enabling and general methods for BCPs synthesis, considering both scope and limitation. Recent breakthroughs on the synthesis of bridge-substituted BCPs are described, as well as methodologies for postsynthesis functionalization. We further explore new challenges and directions for the field, such as the emergence of other rigid small ring hydrocarbons and heterocycles possessing unique substituent exit vectors.
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spelling pubmed-103016822023-06-29 Conquering the Synthesis and Functionalization of Bicyclo[1.1.1]pentanes Shire, Bethany R. Anderson, Edward A. JACS Au [Image: see text] Bicyclo[1.1.1]pentanes (BCPs) have become established as attractive bioisosteres for para-substituted benzene rings in drug design. Conferring various beneficial properties compared with their aromatic “parents,” BCPs featuring a wide array of bridgehead substituents can now be accessed by an equivalent variety of methods. In this perspective, we discuss the evolution of this field and focus on the most enabling and general methods for BCPs synthesis, considering both scope and limitation. Recent breakthroughs on the synthesis of bridge-substituted BCPs are described, as well as methodologies for postsynthesis functionalization. We further explore new challenges and directions for the field, such as the emergence of other rigid small ring hydrocarbons and heterocycles possessing unique substituent exit vectors. American Chemical Society 2023-05-16 /pmc/articles/PMC10301682/ /pubmed/37388694 http://dx.doi.org/10.1021/jacsau.3c00014 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Shire, Bethany R.
Anderson, Edward A.
Conquering the Synthesis and Functionalization of Bicyclo[1.1.1]pentanes
title Conquering the Synthesis and Functionalization of Bicyclo[1.1.1]pentanes
title_full Conquering the Synthesis and Functionalization of Bicyclo[1.1.1]pentanes
title_fullStr Conquering the Synthesis and Functionalization of Bicyclo[1.1.1]pentanes
title_full_unstemmed Conquering the Synthesis and Functionalization of Bicyclo[1.1.1]pentanes
title_short Conquering the Synthesis and Functionalization of Bicyclo[1.1.1]pentanes
title_sort conquering the synthesis and functionalization of bicyclo[1.1.1]pentanes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10301682/
https://www.ncbi.nlm.nih.gov/pubmed/37388694
http://dx.doi.org/10.1021/jacsau.3c00014
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