105748-58-1Relevant articles and documents
Spirocyclization strategy toward indole phytoalexins. The first synthesis of (±)-1-methoxyspirobrassinin, (±)-1-methoxyspirobrassinol, and (±)-1-methoxyspirobrassinol methyl ether
Kutschy, Peter,Suchy, Mojmír,Monde, Kenji,Harada, Nobuyuki,Maru?ková, Renata,?urillová, Zuzana,Dzurilla, Milan,Miklo?ová, Mariana,Mezencev, Roman,Moj?i?, Ján
, p. 9489 - 9492 (2002)
The first syntheses of cruciferous indole phytoalexins (±)-1-methoxyspirobrassinin, (±)-1-methoxyspirobrassinol, (±)-1-methoxyspirobrassinol methyl ether as well as a new syntheses of phytoalexins (±)-spirobrassinin and cyclobrassinin were achieved by dioxane dibromide (DDB)-mediated spirocyclization of brassinin and its 1-substituted derivatives.
A facile method for the synthesis of indole phytoalexin rutalexin
Budovská, Mariana,Kudli?ková, Zuzana,Kutschy, Peter,Pilátová, Martina,Moj?i?, Ján
, p. 3945 - 3947 (2015)
Novel methods for the preparation of the indole phytoalexin rutalexin (8) in high yields are presented. The synthesis of rutalexin (8) was achieved from previously synthesized 9-tert-butoxycarbonyl-2-methoxy-4-oxo-[1,3]thiazino[6,5-b]indole (5) by its hydrolysis, methylation, and deprotection. A second method starting from 9-Boc-cyclobrassinin (9) involved oxidation, methylation, and deprotection.
A concise synthesis of cyclobrassinin and its analogues via a thiyl radical aromatic substitution
Zhong, Xin,Chen, Ning,Xu, Jiaxi
, p. 13549 - 13557 (2018/08/21)
A simple and concise approach for the synthesis of cyclobrassinin has been developed through a thiyl radical-mediated intramolecular aromatic substitution, with benzoyl peroxide as an efficient initiator and oxidant. The current method can also be utilized in the synthesis of 6 and 7-membered ring cyclobrassinin analogues in moderate to good yields. The transformation involves a formal radical 6 and 7-endo-trig cyclization of the corresponding dithiocarbamate derivatives, which were generated from indole-3-methanamines and tryptophan.
New syntheses of indole phytoalexins and related compounds
Kutschy, Peter,Dzurilla, Milan,Takasugi, Mitsuo,Toeroek, Marcel,Achbergerova, Ingrid,Homzova, Renata,Racova, Maria
, p. 3549 - 3566 (2007/10/03)
Synthesis of indole phytoalexins brassinin, brassitin, cyclobrassinin and related compounds via 3-aminomethylindole and its 1-substituted derivatives obtained by nickel boride catalyzed reduction of corresponding aldoximes with sodium borohydride and via [1-(t-butoxycarbonyl)-indol-3-yl]methyl isothiocyanate, the first stable derivative of indol-3-ylmethyl isothiocyanate is described. Antifungal activity of the prepared compounds was examined by using the fungus Bipolaris leersiae by t.l.c. bioassay and quantitative screening was carried out with the selected compounds.