Stereoselective and Regioselective Synthesis of Chiral Dihydrofurocoumarins as Glycohybrids
Priti Kumari1, Ghanshyam Tiwari1, Chintam Narayana1
1Glycochemistry Laboratory, School of Physical Sciences, Jawaharlal Nehru University, New Delhi 110067, India.
Abstract:
Herein, we report a new single-step process for the synthesis of chirally pure dihydrofurocoumarins, demonstrating high regio- and stereoselectivity. This method involves a diverse range of 4-hydroxy coumarin derivatives, which react with various d-glycals in the presence of ceric ammonium nitrate (CAN) at 90 °C to furnish dihydrofurocoumarins within 1 h in a good isolated yield. This developed method possesses several advantages such as its quick reaction time, wide substrate scope, and generation of two new chiral centers along with the inherited chirality of d-glycals, in the final products, enhancing their possible potential applications in medicinal chemistry, material science, and chemical biology.
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