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1,2-Difunctionalized bicyclo[1.1.1]pentanes: Long-sought-after mimetics for ortho/meta-substituted arenes.

ABSTRACT: The development of a versatile platform for the synthesis of 1,2-difunctionalized bicyclo[1.1.1]pentanes to potentially mimic ortho/meta-substituted arenes is described. The syntheses of useful building blocks bearing alcohol, amine, and carboxylic acid functional handles have been achieved from a simple common intermediate. Several ortho- and meta-substituted benzene analogs, as well as simple molecular matched pairs, have also been prepared using this platform. The results of in-depth ADME (absorption, distribution, metabolism, and excretion) investigations of these systems are presented, as well as computational studies which validate the ortho- or meta-character of these bioisosteres.

SUBMITTER: Zhao JX 

PROVIDER: S-EPMC8285974 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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1,2-Difunctionalized bicyclo[1.1.1]pentanes: Long-sought-after mimetics for <i>ortho</i>/<i>meta</i>-substituted arenes.

Zhao Jin-Xin JX   Chang Yu-Xuan YX   He Chi C   Burke Benjamin J BJ   Collins Michael R MR   Del Bel Matthew M   Elleraas Jeff J   Gallego Gary M GM   Montgomery T Patrick TP   Mousseau James J JJ   Nair Sajiv K SK   Perry Matthew A MA   Spangler Jillian E JE   Vantourout Julien C JC   Baran Phil S PS  

Proceedings of the National Academy of Sciences of the United States of America 20210701 28

The development of a versatile platform for the synthesis of 1,2-difunctionalized bicyclo[1.1.1]pentanes to potentially mimic <i>ortho</i>/<i>meta</i>-substituted arenes is described. The syntheses of useful building blocks bearing alcohol, amine, and carboxylic acid functional handles have been achieved from a simple common intermediate. Several <i>ortho-</i> and <i>meta</i>-substituted benzene analogs, as well as simple molecular matched pairs, have also been prepared using this platform. The  ...[more]

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