Qixuan Wang

PhD candidate, Academy for Advanced Interdisciplinary Studies, Peking University

My major is organic synthetic chemistry, specifically in the area of total syntheses of natural products. I have taken the courses of organic chemistry, chemical biology, biochemistry, etc. I am also interested in computer programming. I have some experience in development of websites, C# WinForm programs and python crawlers.


Publications

Divergent total syntheses of ITHQ-type bis-β-carboline alkaloids by regio-selective formal aza-[4 + 2] cycloaddition and late-stage C–H functionalization

Qixuan Wang#, Fusheng Guo, Jin Wang and Xiaoguang Lei*

We herein report the first total syntheses of several bis-β-carboline alkaloids, picrasidines G, S, R, and T, and natural product-like derivatives in a divergent manner. Picrasidines G, S, and T feature an indolotetrahydroquinolizinium (ITHQ) skeleton, while picrasidine R possesses a 1,4-diketone linker between two β-carboline fragments. The synthesis of ITHQ-type bis-β-carboline alkaloids could be directly achieved by a late-stage regio-selective aza-[4 + 2] cycloaddition of vinyl β-carboline alkaloids, suggesting that this remarkable aza-[4 + 2] cycloaddition might be involved in the biosynthetic pathway. Computational studies revealed that such aza-[4 + 2] cycloaddition is a stepwise process and explained the unique regioselectivity (ΔΔG = 3.77 kcal mol−1). Moreover, the successful application of iridium-catalyzed C–H borylation on β-carboline substrates enabled the site-selective C-8 functionalization for efficient synthesis and structural diversification of this family of natural products. Finally, concise synthesis of picrasidine R by the thiazolium-catalyzed Stetter reaction was also accomplished.

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Chem. Sci., 2023, 14, 10353-10359. DOI: 10.1039/d3sc03722c


Education

Peking University

PhD candidate, Integrative Biology (Chemistry)

Supervisor: Prof. Xiaoguang Lei

Research Area: total syntheses of natural products.

Awards & Certifications:

September 2020 - June 2025 (expected)

Skills

  • Primary skill: organic synthesis.
  • English level (CET-4: 587, CET-6: 513)
  • Programming skills: C# WinForm, python, web (HTML + CSS + JS).