Development of a Concise Synthetic Approach to Gliflozin Aglycones from Regioselective Deprotonation of 1,4-Dihalobenzenes
Herein, we report a concise synthetic approach to gliflozin (SGLT2 inhibitors) aglycones from generating regioselective ortho-lithiation based on differentiating the acidifying effect of 1,4-dihalobenzenes and reacting with (hetero)aromatic aldehydes. Then, the resulting diarylmethyl alcohol was converted to diarylmethane using acid-mediated reduction, offering a two-step practical method for synthesizing aglycones of various gliflozins such as Dapagliflozin, Empagliflozin, and Ipragliflozins.
Authors
- Chada Raji Reddy (ORCID: https://orcid.org/0000-0003-1491-7381)
- Manvendra Kumar (ORCID: https://orcid.org/0000-0002-6366-1661)
- Gangarajula Sudhakar (ORCID: https://orcid.org/0000-0003-3498-5584)
- Chennam Ramu
- Thenkrishnan Kumaraguru (ORCID: https://orcid.org/0000-0001-5068-7304)
- Subhash Ghosh (ORCID: https://orcid.org/0000-0002-5877-8910)
- Avula Shivakrishna
Institutions
- Indian Institute of Chemical Technology (IN)
- Academy of Scientific and Innovative Research (IN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-04-28
- DOI
- https://doi.org/10.1021/acs.joc.4c02914
- Primary Topic
- Catalytic Cross-Coupling Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Council of Scientific and Industrial Research, India