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

Maryam Bashir, Muhammad Arshad*, Robina Begum, Varinder k. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

2 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)4281–4285
Number of pages5
JournalOrganic Letters
Volume25
Issue number23
Early online date7 Jun 2023
DOIs
Publication statusPublished - 16 Jun 2023

Bibliographical note

Funding Information:
The authors thank Commonwealth Commission UK under the Split-site Ph.D. Programme (2021-2022) and the Higher Education Commission (HEC), Pakistan, under IRSIP (2022) for generous financial support.

Publisher Copyright:
© 2023 American Chemical Society. All rights reserved.

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