Application of Enantioselective Sulfur Ylide Epoxidation to a Short Asymmetric Synthesis of Bedaquiline, a Potent Anti-Tuberculosis Drug

[Image: see text] A highly selective asymmetric synthesis of a potent anti-TB drug (−)-bedaquiline is accomplished using sulfur ylide asymmetric epoxidation, employing (+)-isothiocineole as an inexpensive and readily available chiral sulfide. Excellent enantioselectivity (er 96:4) and diastereoselec...

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Autores principales: Bashir, Maryam, Arshad, Muhammad, Begum, Robina, Aggarwal, Varinder K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10278180/
https://www.ncbi.nlm.nih.gov/pubmed/37284829
http://dx.doi.org/10.1021/acs.orglett.3c01286
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author Bashir, Maryam
Arshad, Muhammad
Begum, Robina
Aggarwal, Varinder K.
author_facet Bashir, Maryam
Arshad, Muhammad
Begum, Robina
Aggarwal, Varinder K.
author_sort Bashir, Maryam
collection PubMed
description [Image: see text] A highly selective asymmetric synthesis of a potent anti-TB drug (−)-bedaquiline is accomplished using sulfur ylide asymmetric epoxidation, employing (+)-isothiocineole as an inexpensive and readily available chiral sulfide. Excellent enantioselectivity (er 96:4) and diastereoselectivity (dr 90:10) were obtained for the construction of the key diaryl epoxide, which was subsequently subjected to a highly regioselective ring opening (96:4). The synthesis was completed in nine steps starting from commercially available aldehyde in 8% overall yield.
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spelling pubmed-102781802023-06-20 Application of Enantioselective Sulfur Ylide Epoxidation to a Short Asymmetric Synthesis of Bedaquiline, a Potent Anti-Tuberculosis Drug Bashir, Maryam Arshad, Muhammad Begum, Robina Aggarwal, Varinder K. Org Lett [Image: see text] A highly selective asymmetric synthesis of a potent anti-TB drug (−)-bedaquiline is accomplished using sulfur ylide asymmetric epoxidation, employing (+)-isothiocineole as an inexpensive and readily available chiral sulfide. Excellent enantioselectivity (er 96:4) and diastereoselectivity (dr 90:10) were obtained for the construction of the key diaryl epoxide, which was subsequently subjected to a highly regioselective ring opening (96:4). The synthesis was completed in nine steps starting from commercially available aldehyde in 8% overall yield. American Chemical Society 2023-06-07 /pmc/articles/PMC10278180/ /pubmed/37284829 http://dx.doi.org/10.1021/acs.orglett.3c01286 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Bashir, Maryam
Arshad, Muhammad
Begum, Robina
Aggarwal, Varinder K.
Application of Enantioselective Sulfur Ylide Epoxidation to a Short Asymmetric Synthesis of Bedaquiline, a Potent Anti-Tuberculosis Drug
title Application of Enantioselective Sulfur Ylide Epoxidation to a Short Asymmetric Synthesis of Bedaquiline, a Potent Anti-Tuberculosis Drug
title_full Application of Enantioselective Sulfur Ylide Epoxidation to a Short Asymmetric Synthesis of Bedaquiline, a Potent Anti-Tuberculosis Drug
title_fullStr Application of Enantioselective Sulfur Ylide Epoxidation to a Short Asymmetric Synthesis of Bedaquiline, a Potent Anti-Tuberculosis Drug
title_full_unstemmed Application of Enantioselective Sulfur Ylide Epoxidation to a Short Asymmetric Synthesis of Bedaquiline, a Potent Anti-Tuberculosis Drug
title_short Application of Enantioselective Sulfur Ylide Epoxidation to a Short Asymmetric Synthesis of Bedaquiline, a Potent Anti-Tuberculosis Drug
title_sort application of enantioselective sulfur ylide epoxidation to a short asymmetric synthesis of bedaquiline, a potent anti-tuberculosis drug
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10278180/
https://www.ncbi.nlm.nih.gov/pubmed/37284829
http://dx.doi.org/10.1021/acs.orglett.3c01286
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