Hexafluoroisopropanol-Induced Facial Selectivity in a Hindered Diels–Alder Reaction-Reference-Cited by-同舟云学术

Hexafluoroisopropanol-Induced Facial Selectivity in a Hindered Diels–Alder Reaction

Published:2023-01-19 Issue:13 Volume:55 Page:2047-2052
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Kornfilt David J. P.¹^ORCID,Chamberlain Brian T.¹,Wagner Florence F.¹,Chataigner Isabelle²³,Spezia Riccardo²

Affiliation:

1. Center for the Development of Therapeutics, Broad Institute of MIT and Harvard

2. Sorbonne Université, CNRS, Laboratoire de Chimie Théorique

3. Normandie Université, UNIROUEN, CNRS, INSA Rouen, COBRA Laboratory

Abstract

AbstractBRD4780 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.

Funder

Instituto Carlos Slim de la Salud

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/a-2016-4548.pdf

Reference19 articles.

1. Lewis Acid Catalyzed Diels−Alder Reactions of Highly Hindered Dienophiles

2. The Diels-Alder Reaction in Total Synthesis

3. The Catalytic Enantioselective Construction of Molecules with Quaternary Carbon Stereocenters

4. Diels−Alder Exo Selectivity in Terminal-Substituted Dienes and Dienophiles: Experimental Discoveries and Computational Explanations

5. A Rare Kidney Disease To Cure Them All? Towards Mechanism-Based Therapies for Proteinopathies