Journal of Natural Medicines ( IF 3.3 ) Pub Date : 2021-01-03 , DOI: 10.1007/s11418-020-01468-9 Kaori Ryu , Seikou Nakamura , Souichi Nakashima , Hisashi Matsuda
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
中文翻译:
使用萝卜酶从氨基酸一锅对映选择性合成(S)-spirobrassinin和非天然(S)-methylspirobrassinin
摘要
通过着重于十字花科植物中植物抗毒素的产生,实现了具有独特的含硫螺氧杂吲哚骨架的(S)-(-)-spirobrassinin的对映选择性合成。具体地,通过涉及与各种萝卜酶和成分的S-螺环化的反应,即使用萝卜作为反应试剂,催化剂和方法,以1-锅方式从1-色氨酸以单锅方式获得(S)-(-)-螺油菜素。反应容器。令人惊讶地,这种策略也使新的非天然spirooxindole(的一锅对映选择性合成小号) - ( - ) -从5-甲基-5- methylspirobrassinin DL色氨酸。