Total Synthesis of the Neuronal Cell-Protecting Carbazole Alkaloids Carbazomadurin A and (S)-(+)-Carbazomadurin B

被引:24
作者
Hieda, Yuhzo [1 ]
Choshi, Tominari [1 ]
Fujioka, Haruto [1 ]
Hibino, Satoshi [1 ]
机构
[1] Fukuyama Univ, Fac Pharm & Pharmaceut Sci, Fukuyama, Hiroshima 7290292, Japan
基金
日本学术振兴会;
关键词
Total synthesis; Alkaloids; Nitrogen heterocycles; Electrocyclic reactions; Cross-coupling; Configuration determination; CROSS-COUPLING REACTIONS; 1ST TOTAL-SYNTHESIS; ELECTROCYCLIC REACTIONS; MURRAYAQUINONE; CARAZOSTATIN; CALOTHRIXINS; DERIVATIVES; HYELLAZOLE;
D O I
10.1002/ejoc.201301059
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total syntheses of the neuronal cell-protecting carbazole alkaloids carbazomadurin A and (S)-(+)-carbazomadurin B were achieved. The key step of the synthesis of the polysubstituted carbazole rings included an allene-mediated electrocyclic reaction of the 6-electron system that involved the indole 2,3-bond. The cleavage of the alkoxy groups of the resulting 3-ethoxy-8-isopropoxycarbazole successfully gave the 3,8-dihydroxycarbazole, which was converted into the 3,8-bis(OSEM)-carbazole (SEM = 2-trimethylsilylethoxymethyl). A Suzuki-Miyaura cross-coupling reaction of the 3,8-bis(OSEM)-carbazole with the corresponding alkenyl pinacol borates afforded the 1-alkenylcarbazoles, which were treated with tetra-n-butylammonium fluoride (TBAF) followed by reduction with NaBH4 to provide carbazomadurin A and (S)-(+)-carbazomadurin B, respectively.
引用
收藏
页码:7391 / 7401
页数:11
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