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

Autor: Jin-Xin Zhao, Yu-Xuan Chang, Chi He, Burke, Benjamin J., Collins, Michael R., Del Bel, Matthew, Elleraas, Jeff, Gallegoc, Gary M., Montgomery, T. Patrick, Mousseau, James J., Nairc, Sajiv K., Perry, Matthew A., Spangler, Jillian E., Vantourout, Julien C., Baran, Phil S.
Předmět:
Zdroj: Proceedings of the National Academy of Sciences of the United States of America; 7/13/2021, Vol. 118 Issue 28, p1-5, 5p
Abstrakt: 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 orthoor meta-character of these bioisosteres. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index