Organocatalytic Enantioselective Conjugate Addition of Nitromethane to Benzylidene-2-Benzoyl Acetate: Asymmetric Synthesis of ABT – 627, an Endothelin Receptor Antagonist

Saumen Hajra; Sk Mohammad Aziz; Bibekananda Jana; Bibekananda Jana; Sunit Hazra

doi:10.3389/fchem.2020.00135

Frontiers in Chemistry (Mar 2020)

Organocatalytic Enantioselective Conjugate Addition of Nitromethane to Benzylidene-2-Benzoyl Acetate: Asymmetric Synthesis of ABT – 627, an Endothelin Receptor Antagonist

Saumen Hajra,
Sk Mohammad Aziz,
Bibekananda Jana,
Bibekananda Jana,
Sunit Hazra

Affiliations

Saumen Hajra: Centre of Biomedical Research, Sanjay Gandhi Post-Graduate Institute of Medical Sciences, Lucknow, India
Sk Mohammad Aziz: Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur, India
Bibekananda Jana: Centre of Biomedical Research, Sanjay Gandhi Post-Graduate Institute of Medical Sciences, Lucknow, India
Bibekananda Jana: Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur, India
Sunit Hazra: Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur, India

DOI: https://doi.org/10.3389/fchem.2020.00135
Journal volume & issue: Vol. 8

Abstract

Read online

First catalytic and enantioselective conjugate addition of nitromethane to benzylidene-2-benzoyl acetate has been developed using dihydroquinine derived squaramide catalyst with moderate to high selectivities. Asymmetric total synthesis of ABT-627, a potent ETA receptor antagonist is accomplished utilizing the developed method in overall 15.7% yield.

Published in Frontiers in Chemistry

ISSN: 2296-2646 (Online)
Publisher: Frontiers Media S.A.
Country of publisher: Switzerland
LCC subjects: Science: Chemistry
Website: http://journal.frontiersin.org/journal/chemistry

About the journal

Abstract

Keywords