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1,2-Difunctionalized Bicyclo[1.1.1]pentanes: Long Sought After Bioisosteres for ortho/meta-Substituted Arenes

preprint
submitted on 21.10.2020, 01:10 and posted on 21.10.2020, 10:39 by Jin-Xin Zhao, Yuxuan Chang, Jeff Elleraas, T. Patrick Montgomery,, Jillian E. Spangler, Sajiv K. Nair, Matthew Del Bel, Gary M. Gallego, James J. Mousseau, Matthew A. Perry, Michael R. Collins, Julien Vantourout, Phil Baran

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 synthesis of useful building blocks bearing alcohol, amine, and carboxylic acid functional handles has been achieved from a simple common intermediate. Several ortho and/or meta-substituted benzene analogues as well as simple molecular matched pairs have also been prepared using this platform. In-depth biological and computational studies are currently in progress to validate the ortho and/or meta-character of these new bioisosteres. Results of these investigations will be reported in due course.

Funding

Pfizer

NIH (GM-118176)

History

Email Address of Submitting Author

pbaran@scripps.edu

Institution

Scripps Research

Country

USA

ORCID For Submitting Author

0000-0001-9193-9053

Declaration of Conflict of Interest

No conflict of interest

Version Notes

Version 1.0

Exports