Synthesis of naturally occurring naphthoquinone epoxides and application in the synthesis of β-lapachone

被引:13
作者
Claessens, Sven [1 ]
Habonimana, Pascal [1 ]
De Kimpe, Norbert [1 ]
机构
[1] Univ Ghent, Dept Organ Chem, Fac Biosci Engn, B-9000 Ghent, Belgium
关键词
PROSTATE-CANCER CELLS; MOLLUSCICIDAL ACTIVITY; TRYPANOCIDAL ACTIVITY; INDUCED APOPTOSIS; EPOXIDATION; INDUCTION; OXIDATION; QUINONES; KETONES; DRUGS;
D O I
10.1039/c004580b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Optimized epoxidation conditions of mono- and dialkylated naphthoquinones are presented. Based on the epoxidation protocol making use of H2O2/Na2CO3, naphthoquinone epoxides are obtained in high yields. The optimized epoxidation conditions are applied in a short and high yielding synthesis of the pharmaceutically important beta-lapachone.
引用
收藏
页码:3790 / 3795
页数:6
相关论文
共 50 条
[41]   SYNTHESIS, STRUCTURE AND REACTIONS OF ALPHA-CAMPHOLENIC EPOXIDES [J].
SCHULZE, K ;
HABERMANN, AK ;
UHLIG, H ;
WEBER, L ;
KEMPE, R .
LIEBIGS ANNALEN DER CHEMIE, 1993, (09) :987-991
[42]   Mild Iridium-Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β-Alkyl Amines [J].
Cabre, Albert ;
Cabezas-Gimenez, Juanjo ;
Sciortino, Giuseppe ;
Ujaque, Gregori ;
Verdaguer, Xavier ;
Lledos, Agusti ;
Riera, Antoni .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (15) :3624-3631
[43]   Stereoselective synthesis of trisubstituted epoxides via cobalt catalysis [J].
Bao, Honghao ;
Shi, Yixiang ;
Zhang, Junliang ;
Yang, Junfeng ;
Wu, Junliang .
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (18) :4932-4936
[44]   Synthesis of functionalised isochromans: epoxides as aldehyde surrogates in hexafluoroisopropanol [J].
Muller, Cyprien ;
Horky, Filip ;
Vayer, Marie ;
Golushko, Andrei ;
Leboeuf, David ;
Moran, Joseph .
CHEMICAL SCIENCE, 2023, 14 (11) :2983-2989
[45]   Synthesis of novel naphthoquinone aliphatic amides and esters and their anticancer evaluation [J].
Kongkathip, Boonsong ;
Akkarasamiyo, Sunisa ;
Hasitapan, Komkrit ;
Sittikul, Pichamon ;
Boonyalai, Nonlawat ;
Kongkathip, Ngampong .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 60 :271-284
[46]   Synthesis, Biological, and Computational Study of Naphthoquinone Derivatives Containing Heteroatoms [J].
Bayrak, Nilufer ;
Yildirim, Hatice ;
Tuyun, Amac Fatih ;
Kara, Emel Mataraci ;
Celik, Berna Ozbek ;
Gupta, Girish Kumar .
JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2016, 38 (06) :1211-1221
[47]   Stereoselective Synthesis of Trisubstituted Epoxides Marks the Route to Chiral Building Blocks with Quaternary Centers [J].
Garcia-Castro, Miguel ;
Annamalai, Murali ;
Golz, Christopher ;
Strohmann, Carsten ;
Kumar, Kamal .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (37) :5660-5665
[48]   Synthesis and biological evaluation of N-alkyl naphthoimidazoles derived from β-lapachone against Trypanosoma cruzi bloodstream trypomastigotes [J].
da Silva, Ari Miranda ;
Araujo-Silva, Leonardo ;
Bombaca, Ana Cristina S. ;
Menna-Barreto, Rubem F. S. ;
Rodrigues-Santos, Claudio Eduardo ;
Buarque Ferreira, Aurelio B. ;
de Castro, Solange L. .
MEDCHEMCOMM, 2017, 8 (05) :952-959
[49]   Development of recyclable chiral macrocyclic metal complexes for asymmetric aminolysis of epoxides: application for the synthesis of an enantiopure oxazolidine ring [J].
Tak, Raj Kumar ;
Kumar, Manish ;
Nazish, Mohd ;
Menapara, Tushar Kumar ;
Kureshy, Rukhsana, I ;
Khan, Noor-ul H. .
NEW JOURNAL OF CHEMISTRY, 2018, 42 (18) :15325-15331
[50]   Synthesis and HHDH-Catalyzed Kinetic Resolution of Propargylic Epoxides [J].
Kolman, Robert J. ;
Svaco, Petra ;
Elenkov, Maja Majeric ;
Dokli, Irena .
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (24) :5066-5072