Total synthesis of (-)-indolactam V.
Total synthesis of (-)-indolactam V.
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DOI：
10.1039/c0ob01115k
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发表时间：
2011-03
影响因子：
3.2
通讯作者：
Zhengren Xu;Fengying Zhang;Li-he Zhang;Yanxing Jia
中科院分区：
文献类型：
--
作者：
Zhengren Xu;Fengying Zhang;Li-he Zhang;Yanxing Jia
以4-硝基色氨酸衍生物4为关键中间体，经8步反应（总收率49%）和12步反应（总收率18%）成功地合成了蛋白激酶C激活剂（-）-吲哚内酰胺V（IL-V）。3-硝基-2-碘苯胺5分别与醛6和7通过Pd催化吲哚合成反应合成了衍生物3和4，它们都含有吲哚4-取代和IL-V中的C-9立体中心。同时，以L-谷氨酸为原料，经5步反应合成了醛7，产率为68%。在THF中使用HATU以良好的产率实现9元环的内酰胺化。
The total synthesis of protein kinase C activator (-)-indolactam V (IL-V) has been successfully completed with two separate approaches: From known 4-nitrotryptophan derivative 3 in 8 steps (49% overall yield) and from L-glutamic acid in 12 steps (18% overall yield), where 4-nitrotryptophanol derivative 4 served as a key intermediate. Derivatives 3 and 4, both incorporating indole 4-substitution and the C-9 stereocenter in IL-V, were synthesized via the Pd-catalyzed indole synthesis from 3-nitro-2-iodoaniline 5 with aldehydes 6 and 7, respectively. Aldehyde 7 was, meanwhile, synthesized from l-glutamic acid in 5 steps (68% yield). Lactamization of the 9-membered ring was achieved using HATU in THF in good yield.