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Synthesis 2023; 55(13): 2047-2052
DOI: 10.1055/a-2016-4548
DOI: 10.1055/a-2016-4548
paper
Hexafluoroisopropanol-Induced Facial Selectivity in a Hindered Diels–Alder Reaction
Authors
This work was funded by the Slim Initiative for Genomic Medicine in the Americas (SIGMA), a collaboration of the Broad Institute with the Carlos Slim Foundation.
Abstract
BRD4780 is a small molecule that can selectively clear mutant MUC1-fs protein in mucin kidney disease models. Prior syntheses of BRD4780 were unsuitable for preparation on large scale. In this manuscript, HFIP is described as a unique solvent that allowed the key Diels–Alder reaction to proceed with >20:1 endo diastereoselectivity, enabling the kg-scale preparation of BRD4780 for further studies.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2016-4548.
- Supporting Information (PDF)
Publication History
Received: 14 December 2022
Accepted after revision: 19 January 2023
Accepted Manuscript online:
19 January 2023
Article published online:
20 March 2023
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