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
收藏
页码：4281 / 4285
页数：5
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