19676-67-6Relevant academic research and scientific papers
TREATMENT OR PREVENTION OF LEUKAEMIA
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Page/Page column 15-16, (2021/04/23)
The present invention provides compounds for use in the treatment or prevention of leukaemia which are based on a 2-amino-[1,1']-bipbenyl or corresponding carbazole scaffold, in particular, it provides the following compounds of formula (I), their stereoi
Hit to Leads with Cytotoxic Effect in Leukemic Cells: Total Synthesis Intermediates as a Molecule Treasure Chest
Bj?rsvik, Hans-René,Gjertsen, Bj?rn Tore,Elumalai, Vijayaragavan
, p. 862 - 870 (2020/05/05)
A previously designed and developed 12-step total synthesis that includes [1,1′-biphenyl]-2-amine and carbazole intermediates and that ultimately produces the carbazole alkaloid carbazomycin G was exploited as a screening compound library with the goal of
Carbazomycin G: Method Development and Total Synthesis
Elumalai, Vijayaragavan,Gambarotti, Cristian,Bj?rsvik, Hans-René
, p. 1984 - 1992 (2018/05/15)
A novel total synthesis leading to the carbazole alkaloid carbazomycin G was designed and developed. The outlined synthetic route is composed of twelve synthetic steps including the transformations of the initial simple substrate and intermediates. To rea
Broadly Applicable Stereoselective Syntheses of Serrulatane, Amphilectane Diterpenes, and Their Diastereoisomeric Congeners Using Asymmetric Hydrovinylation for Absolute Stereochemical Control
Tenneti, Srinivasarao,Biswas, Souvagya,Cox, Glen Adam,Mans, Daniel J.,Lim, Hwan Jung,RajanBabu
, p. 9868 - 9881 (2018/07/25)
A stereogenic center, placed at an exocyclic location next to a chiral carbon in a ring to which it is attached, is a ubiquitous structural motif seen in many bioactive natural products, including di- and triterpenes and steroids. Installation of these ce
Enantioselective Synthesis of (+)-Mitomycin K by a Palladium-Catalyzed Oxidative Tandem Cyclization
Gu, Qiang-Shuai,Yang, Dan
, p. 5886 - 5889 (2017/05/12)
The mitomycins, a family of bioactive natural products, feature a compact 6/5/5-fused polycyclic ring structure densely decorated with highly reactive and/or fragile quinone, amino ketal, and aziridine as well as carbamate moieties. It is this striking feature that has defeated numerous synthetic attempts towards these apparently small molecules, rendering them one of the most formidable targets for total synthesis. We herein report the first enantioselective synthesis of (+)-mitomycin K, a representative of G series mitomycins. The key step of this synthesis is an enantioselective oxidative cyclization catalyzed by a palladium/(+)-sparteine system that had previously been developed by our group. The robustness of this method bodes well for further applications in the asymmetric total synthesis of natural products, particularly those with characteristic 6/5/5-fused pyrroloindole skeletons.
Synthesis of a leucomitosane via a diastereoselective radical cascade
Brucelle, Francois,Renaud, Philippe
, p. 6245 - 6252 (2013/07/26)
The preparation of trans-2,3-disubstituted indolines from 1-azido-2-allylbenzene derivatives via a diastereoselective radical cascade using ethyl iodoacetate and triethylborane is described. Further lactamization afforded substituted benzopyrrolizidinones
Total synthesis of (-)-lemonomycin
Yoshida, Atsushi,Asakawa, Tomohiro,Hamashima, Yoshitaka,Kan, Toshiyuki,Akaiwa, Michinori,Yokoshima, Satoshi,Fukuyama, Tohru
, p. 11192 - 11195,4 (2012/12/12)
When life gives you lemons: An efficient and convergent enantioselective total synthesis of (-)-lemonomycin, which shows potent activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VREF), is presented. The key reaction steps are a Hosomi-Sakurai-type cyclization, a thermodynamically controlled Pictet-Spengler reaction, and a glycosidation reaction with lemonose (see scheme). Copyright
Synthesis of the ABH rings of ecteinascidin 597 using a connective Pummerer-type cyclisation
Smith, Laura H. S.,Nguyen, Trung Thanh,Sneddon, Helen F.,Procter, David J.
, p. 10821 - 10823 (2011/11/05)
A connective Pummerer-type cyclisation involving a cysteine derivative and an N-benzyl glyoxamide 3 has been applied in an asymmetric synthesis of the protected ABH rings 2 of the antitumour and antimicrobial natural product ecteinascidin 597.
PRODRUGS OF OXAZOLIDINONE CETP INHIBITORS
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Page/Page column 9, (2010/04/27)
The compounds of Formula I are prodrugs of CETP inhibitors having a central oxazolidinone ring. The compounds cyclize by the elimination of HX to form an oxazolidinone ring after administration to a patient.
Synthetic studies on (-)-lemonomycin: An efficient asymmetric synthesis of lemonomycinone amide
Wu, Yan-Chao,Bernadat, Guillaume,Masson, Geraldine,Couturier, Cedric,Schlama, Thierry,Zhu, Jieping
supporting information; experimental part, p. 2046 - 2052 (2009/08/07)
Asymmetric synthesis of lemonomycinone amide (2) was accomplished from readily accessible starting materials. Enantioselective alkylation of N-(diphenylmethylene)glycine tert-butyl ester (11) by 5-tert- butyldimethylsilyloxy-2,4-dimethoxy-3-methylbenzyl bromide (10) in the presence of Corey-Lygo's phase transfer catalyst [O-(9)-ally-N-(9-anthracenylmethyl) cinchonidium bromide, 0.1 equiv] afforded, after chemoselective hydrolysis of the imine function (THF/H2O/AcOH), the substituted L-tert-butyl phenylalanate 13 in 85% yield. A Pictet-Spengler reaction of 14 with benzyloxyacetaldehyde (15) provided the 1,3-cisdisubstituted tetrahydroisoquinoline 16 in 85% yield as a single diastereomer. Coupling of hindered secondary amine 16 with amino acid 9 was accomplished under carefully controlled conditions to furnish the amide 22, which was in turn converted to hemiaminal 24. A hafnium triflate catalyzed conversion of hemiaminal to α-amino thioether followed by a silver tetrafluoroborate promoted intramolecular Mannich reaction of 26 afforded the tetracycle 27 in excellent overall yields. Debenzylation of 27 [Pd(OH)2, H2, MeOH, 0°C], removal of N-Boc function (aqueous 3 N HCl, MeOH/H2O), and oxidation of hydroquinone to quinone [(NH4)2Ce(NO 3)6, H2O, rt] afforded the lemonomycinone amide 2 in 76% yield over three steps
