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

Bashir, Maryam; Arshad, Muhammad; Begum, Robina; Aggarwal, Varinder K.

Afiliación

Bashir M; School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K.
Arshad M; Centre for Organic Chemistry, School of Chemistry, University of the Punjab, Lahore 54590, Pakistan.
Begum R; Institute of Chemistry, The Islamia University of Bahawalpur, Bahawalpur 63100, Pakistan.
Aggarwal VK; Centre for Organic Chemistry, School of Chemistry, University of the Punjab, Lahore 54590, Pakistan.

Org Lett ; 25(23): 4281-4285, 2023 06 16.

Article en En | MEDLINE | ID: mdl-37284829

RESUMEN

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.

Asunto(s)

Antituberculosos; Azufre; Estructura Molecular; Estereoisomerismo

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Azufre / Antituberculosos Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2023 Tipo del documento: Article Pais de publicación: Estados Unidos

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