One-pot enantioselective synthesis of (S)-spirobrassinin and non-natural (S)-methylspirobrassinin from amino acids using a turnip enzyme
One-pot enantioselective synthesis of (S)-spirobrassinin and non-natural (S)-methylspirobrassinin from amino acids using a turnip enzyme
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DOI：
10.1007/s11418-020-01468-9
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发表时间：
2021-01
影响因子：
3.3
通讯作者：
Kaori Ryu;Seikou Nakamura;Souichi Nakashima;H. Matsuda
中科院分区：
文献类型：
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作者：
Kaori Ryu;Seikou Nakamura;Souichi Nakashima;H. Matsuda
摘要通过研究十字花科植物中植物保卫素的生成，实现了具有独特含硫螺氧吲哚骨架的(S)-(−)-螺菜素的对映选择性合成。具体来说，(S)-(−)-螺油菜素是以色氨酸为原料，通过与各种萝卜酶和成分进行S-螺环反应，即以萝卜为反应试剂、催化剂和反应容器，一锅法合成的。令人惊讶的是，这一策略还实现了以5-甲基-dl-色氨酸为原料，一锅法合成新型非天然螺氧吲哚(S)-(−)-5-甲基螺菜素。
AbstractThe 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 froml-tryptophan through a reaction involvingS-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