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Alstoscholarisines H–J, Indole Alkaloids from Alstonia scholaris: Structural Evaluation and Bioinspired Synthesis of Alstoscholarisine H

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posted on 22.01.2016, 00:00 by Zhiqiang Pan, Xu-Jie Qin, Ya-Ping Liu, Ting Wu, Xiao-Dong Luo, Chengfeng Xia
Alstoscholarisines H–J (13), new monoterpenoid indole alkaloids with an unprecedented skeleton created via the formation of a C-3/N-1 bond, were isolated from Alstonia scholaris. Their structures were established by extensive spectroscopic analyses and the assessment of single-crystal X-ray diffraction data. The total synthesis of alstoscholarisine H was achieved via the regioselective nucleophilic addition of pyridinium through a bioinspired iminium ion intermediate followed by Pictet–Spengler-like cyclization.