105748-59-2Relevant articles and documents
One-pot enantioselective synthesis of (S)-spirobrassinin and non-natural (S)-methylspirobrassinin from amino acids using a turnip enzyme
Ryu, Kaori,Nakamura, Seikou,Nakashima, Souichi,Matsuda, Hisashi
, p. 308 - 318 (2021/01/07)
Abstract: The enantioselective synthesis of (S)-(?)-spirobrassinin, which features a unique sulfur-containing spirooxindole skeleton, was achieved by focusing on the phytoalexin generation in Brassicaceae plants. Specifically, (S)-(?)-spirobrassinin was obtained in a one-pot fashion from l-tryptophan through a reaction involving S-spirocyclization with various turnip enzymes and constituents, i.e., using the turnip as a reaction reagent, catalyst, and reaction vessel. Surprisingly, this strategy also enabled the one-pot enantioselective synthesis of the novel non-natural spirooxindole (S)-(?)-5-methylspirobrassinin from 5-methyl-dl-tryptophan. Graphic abstract: [Figure not available: see fulltext.]
A novel palladium-catalyzed cyclization of indole phytoalexin brassinin and its 1-substituted derivatives
Budovska, Mariana
, p. 5575 - 5582 (2014/01/23)
A novel simple synthetic approach to spiroindoline phytoalexins and their derivatives has been developed. The spirocyclization of brassinin and its 1-substituted derivatives was achieved using palladium catalyst PdCl 2(CH3CN)2 in DMSO at 80°C in the presence of water, methanol or aniline.
Toward the control of Leptosphaeria maculans: Design, syntheses, biological activity, and metabolism of potential detoxification inhibitors of the crucifer phytoalexin brassinin
Pedras, M. Soledade C.,Jha, Mukund
, p. 4958 - 4979 (2007/10/03)
Brassinin (1), a crucial plant defense produced by crucifers, is detoxified by the phytopathogenic fungus Leptosphaeria maculans (Phoma lingam) to indole-3-carboxaldehyde using a putative brassinin oxidase. Potential inhibitors of brassinin detoxification
