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
相关论文
共 34 条
  • [21] Organocatalytic enantioselective synthesis of 1,3,5-polyols by means of iterative asymmetric epoxidation: their application to the total synthesis of polyrhacitide A
    Kumaraswamy, Gullapalli
    Murthy, Akula Narayana
    Sadaiah, Kadivendi
    TETRAHEDRON, 2012, 68 (15) : 3179 - 3186
  • [22] SHORT ENANTIOSELECTIVE SYNTHESIS OF (-)-OVALICIN, A POTENT INHIBITOR OF ANGIOGENESIS, USING SUBSTRATE-ENHANCED CATALYTIC ASYMMETRIC DIHYDROXYLATION
    COREY, EJ
    GUZMANPEREZ, A
    NOE, MC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) : 12109 - 12110
  • [23] Short enantioselective synthesis of (-)-ovalicin, a potent inhibitor of angiogencsis, using substrate-enhanced catalytic asymmetric dihydroxylation
    1600, (116):
  • [24] Application of sulfur ylide mediated epoxidations in the asymmetric synthesis of β-hydroxy-δ-lactones.: Synthesis of a mevinic acid analogue and (+)-prelactone B
    Aggarwal, VK
    Bae, I
    Lee, HY
    TETRAHEDRON, 2004, 60 (43) : 9725 - 9733
  • [25] Polymeric emulsion and crosslink-mediated synthesis of super-stable nanoparticles as sustained-release anti-tuberculosis drug carriers
    Choonara, Yahya E.
    Pillay, Viness
    Ndesendo, Valence M. K.
    du Toit, Lisa C.
    Kumar, Pradeep
    Khan, Riaz A.
    Murphy, Caragh S.
    Jarvis, Debbie-Leigh
    COLLOIDS AND SURFACES B-BIOINTERFACES, 2011, 87 (02) : 243 - 254
  • [26] Sonochemical synthesis and fabrication of honeycomb like zirconium dioxide with chitosan modified electrode for sensitive electrochemical determination of anti-tuberculosis (TB) drug
    Chen, Tse-Wei
    Vasantha, Airathevar Sivasamy
    Chen, Shen-Ming
    Al Farraj, Dunia A.
    Elshikh, Mohamed Soliman
    Alkufeidy, Roua M.
    Al Khulaifi, Manal M.
    ULTRASONICS SONOCHEMISTRY, 2019, 59
  • [27] Whole-genome sequencing-based epidemiological analysis of anti-tuberculosis drug resistance genes in Japan in 2007: Application of the Genome Research for Asian Tuberculosis (GReAT) database
    Takemasa Takii
    Kouhei Seki
    Yasutaka Wakabayashi
    Yuta Morishige
    Tsuyoshi Sekizuka
    Akifumi Yamashita
    Kengo Kato
    Kazuhiro Uchimura
    Akihiro Ohkado
    Naoto Keicho
    Satoshi Mitarai
    Makoto Kuroda
    Seiya Kato
    Scientific Reports, 9
  • [28] Whole-genome sequencing-based epidemiological analysis of anti-tuberculosis drug resistance genes in Japan in 2007: Application of the Genome Research for Asian Tuberculosis (GReAT) database
    Takii, Takemasa
    Seki, Kouhei
    Wakabayashi, Yasutaka
    Morishige, Yuta
    Sekizuka, Tsuyoshi
    Yamashita, Akifumi
    Kato, Kengo
    Uchimura, Kazuhiro
    Ohkado, Akihiro
    Keicho, Naoto
    Mitarai, Satoshi
    Kuroda, Makoto
    Kato, Seiya
    SCIENTIFIC REPORTS, 2019, 9 (1)
  • [29] Asymmetric Synthesis of Anti-tuberculosis-specific Drug TBAJ-876 through Synergistic Li/Li Catalysis
    Li, Jing
    Gao, Feng
    Ahmad, Tanveer
    Luo, Yicong
    Zhang, Zhenfeng
    Yuan, Qianjia
    Zhang, Wanbin
    CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (11): : 1319 - 1326
  • [30] Ultrasonication-ionic liquid synergy for the synthesis of new potent anti-tuberculosis 1,2,4-triazol-1-yl-pyrazole based spirooxindolopyrrolizidines
    Pogaku, Vinay
    Krishna, Vagolu Siva
    Sriram, Dharmarajan
    Rangan, Krishnan
    Basavoju, Srinivas
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2019, 29 (13) : 1682 - 1687
1234