Regioselective (3 + 2) cycloaddition reactions of zerumbone: synthesis of isoxazolines and spiro-pyrrolizidino-oxindoles, conformational diversity and theoretical insights
Regioselective (3 + 2) cycloaddition reactions of zerumbone with nitrile oxides and azomethine ylides are developed for the first time. Direct functionalization of the C10-C11 double bond in zerumbone is unique. ZI-8, ZI-9, and ZI-10 exhibited substrate-driven dimer formation, whereas ZI-9 and ZI-10 exhibited solid-state conformational variability. Furthermore, the reactivity of the C2-C3 double bond was investigated utilizing an azomethine ylide in a three-component strategy. According to theoretical studies, cycloaddition occurs preferentially on the bottom face of double bonds. This work describes a method for site-selective modification of zerumbone and zerumbone epoxide.
Authors
- Mohamad Akbar Ali (ORCID: https://orcid.org/0000-0003-3813-631X)
- Pushparathinam Gopinath (ORCID: https://orcid.org/0000-0002-6577-2357)
- Naga Venkateswara Rao Nulakani (ORCID: https://orcid.org/0000-0002-1127-3069)
- Tanay Kundu (ORCID: https://orcid.org/0000-0002-6871-2894)
- Nandha Kumar Murthi
Institutions
- SRM Institute of Science and Technology (IN)
- Khalifa University of Science and Technology (AE)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob00840a
- Citations
- 1
- Primary Topic
- Ginger and Zingiberaceae research
- Type
- article
- Field-Weighted Citation Impact
- 1.56
Funders
- SRM Institute of Science and Technology
- Department of Science and Technology, Ministry of Science and Technology, India