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

Organic Letters
Zhi-Qiang PanCheng-Feng Xia

Abstract

Alstoscholarisines H-J (1-3), 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.

References

Aug 10, 1973·The Journal of Organic Chemistry·L J Dolby, S J Nelson
Jul 11, 2002·Journal of the American Chemical Society·Shinji Yamada, Chisako Morita
Mar 30, 2007·Organic Letters·Xiang-Hai CaiXiao-Dong Luo
Jan 22, 2008·Organic Letters·Xiang-Hai CaiXiao-Dong Luo
Sep 30, 2008·Journal of the American Chemical Society·Guillaume Barbe, André B Charette
Jul 18, 2009·Planta medica·Tao FengXiao-Dong Luo
Dec 24, 2009·Angewandte Chemie·James J MousseauAndré B Charette
Mar 12, 2010·Journal of Ethnopharmacology·Jian-Hua ShangXiao-Dong Luo
Apr 13, 2010·Journal of Ethnopharmacology·Jian-Hua ShangXiao-Dong Luo
Apr 2, 2011·Angewandte Chemie·Thibaud GerfaudJieping Zhu
Jan 28, 2012·Journal of the American Chemical Society·Gregory L AdamsAmos B Smith
Dec 28, 2012·Journal of the American Chemical Society·Gregory L AdamsAmos B Smith
Feb 13, 2013·Chemistry : a European Journal·Tsugunori WatanabeTsunehiko Higuchi
Aug 24, 2013·Journal of the American Chemical Society·Myles W Smith, Scott A Snyder
Mar 7, 2014·Journal of the American Chemical Society·Joel M SmithNeil K Garg
Oct 30, 2014·Organic Letters·Xing-Wei YangXiao-Dong Luo
Aug 19, 2015·Natural Products and Bioprospecting·Xu-Jie QinXiao-Dong Luo

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Citations

Oct 29, 2017·Journal of Asian Natural Products Research·Yan-Fei Liu, Shi-Shan Yu
Aug 23, 2018·Chemistry & Biodiversity·Jian ZhangXiao-Qi Zhang

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