1362063-20-4Relevant academic research and scientific papers
Total synthesis of (-)-isatisine A via a biomimetic benzilic acid rearrangement
Xiao, Mingxing,Wu, Wei,Wei, Lin,Jin, Xiaojie,Yao, Xiaojun,Xie, Zhixiang
, p. 3705 - 3714 (2015/05/20)
The biomimetic total synthesis of potential anti-HIV (-)-isatisine A, a novel alkaloid with an unprecedented fused tetracyclic skeleton, was accomplished in eight steps from indole and known 4,6-O-isopropylidene-protected glucal. The synthetic strategy was inspired primarily by the proposed biogenetic hypothesis that indole C-furanoside would be derived from indole C-glucoside via a ring contractive benzilic acid rearrangement. The biogenetic hypothesis was enabled by model studies: the O-glucoside was converted to O-furanoside via a benzilic acid rearrangement.
Biomimetic total synthesis of (-)-isatisine a
Wu, Wei,Xiao, Mingxing,Wang, Jiangbing,Li, Ying,Xie, Zhixiang
, p. 1624 - 1627 (2012/05/04)
The biomimetic total synthesis of (-)-isatisine A, a novel alkaloid with an unprecedented fused tetracyclic skeleton, was accomplished in 8 steps from indole and 4,6-O-isopropylidene-protected glucal. The synthesis features a convergent synthetic strategy which relies on nucleophilic addition and a biomimetic benzilic ester rearrangement as key reactions.
