Synthesis of Bridged Alkaloid-like Scaffolds through Sequential Rearrangement of Sulfur Ylides and 2-Hydroxy-β-nitrostyrenes
A two-component, three-molecule cascade reaction between sulfur ylides and 2-hydroxy-β-nitrostyrenes is developed for the efficient and stereoselective synthesis of complex polycyclic alkaloid-like scaffolds. This metal-free protocol proceeds smoothly under mild conditions using readily available materials, affording structurally diverse products in good yields with excellent diastereoselectivity. A plausible mechanism is proposed.
Authors
- Zihan Yan (ORCID: https://orcid.org/0000-0001-5298-4839)
- Wenteng Chen (ORCID: https://orcid.org/0000-0001-9366-3679)
- Jiaan Shao (ORCID: https://orcid.org/0000-0001-8735-3236)
- Haifeng Li (ORCID: https://orcid.org/0000-0002-1953-1210)
- Jian Cui (ORCID: https://orcid.org/0000-0003-1371-4945)
- Jie Cen (ORCID: https://orcid.org/0009-0002-4075-9364)
- Mohan Guo
Institutions
- City University (BD)
- Jinhua Academy of Agricultural Sciences (CN)
- State Institute for Drug Control (CZ)
- Pharmaceutical Biotechnology (Czechia) (CZ)
- Indiana University School of Medicine
- Hangzhou City University
- Zhejiang University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-04-20
- DOI
- https://doi.org/10.1021/acs.joc.6c00376
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Natural Science Foundation of Changzhou City
- National Natural Science Foundation of China
- Natural Science Foundation of Zhejiang Province