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

被引：1

作者：

Bashir, Maryam ^{[1
,2
]}

Arshad, Muhammad ^{[3
]}

Begum, Robina ^{[2
]}

Aggarwal, Varinder K. ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, England

[2] Univ Punjab, Ctr Organ Chem, Sch Chem, Lahore 54590, Pakistan

[3] Islamia Univ Bahawalpur, Inst Chem, Bahawalpur 63100, Pakistan

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 23期

关键词：

MEDIATED EPOXIDATION; ATP SYNTHASE; TUBERCULOSIS; SELECTIVITY; SCOPE;

D O I：

10.1021/acs.orglett.3c01286

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly selectiveasymmetric synthesis of a potent anti-TB drug(-)-bedaquiline is accomplished using sulfur ylide asymmetricepoxidation, employing (+)-isothiocineole as an inexpensive and readilyavailable chiral sulfide. Excellent enantioselectivity (er 96:4) anddiastereoselectivity (dr 90:10) were obtained for the constructionof the key diaryl epoxide, which was subsequently subjected to a highlyregioselective ring opening (96:4). The synthesis was completed innine steps starting from commercially available aldehyde in 8% overallyield.

引用

页码：4281 / 4285

页数：5

共 34 条

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