Total synthesis of marine sponge bis(indole) alkaloids of the topsentin class
Total synthesis of marine sponge bis(indole) alkaloids of the topsentin class
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DOI：
10.1021/jo070286r
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发表时间：
2007-05-11
影响因子：
3.6
通讯作者：
Denis, Jean-Noel
中科院分区：
文献类型：
--
作者：
Guinchard, Xavier;Vallee, Yannick;Denis, Jean-Noel
[图]描述了四种天然双（吲哚）生物碱topsentin 1和2类的合成。它们的双（吲哚）α -羰基咪唑啉和随后的双（吲哚）α -羰基咪唑基团是通过吲哚- α -酮硫咪酯盐4和1-（吲哚-3′-基）-1,2-二氨基乙烷3缩合而成的。该化合物是由-氨基吲哚羟胺5经过两步合成的。这是化合物1d、2a和2b的首次全合成。
[GRAPHICS]The synthesis of four natural bis(indole) alkaloids of topsentin class 1 and 2 is described. Their bis(indole) alpha-carbonylimidazoline and subsequently bis(indole) alpha-carbonylimidazole moieties have been built via the condensation between indolic alpha-ketothioimidate salts 4 and 1-(indol-3'-yl)-1,2-diaminoethane 3. This compound results from the beta-amino indolic hydroxylamine 5 by a two-step sequence. This is the first total synthesis of compounds 1d, 2a, and 2b.