ol5b02085_si_006.cif (2.29 MB)

Synthesis of Bis-pyrrolizidine-Fused Dispiro-oxindole Analogues of Curcumin via One-Pot Azomethine Ylide Cycloaddition: Experimental and Computational Approach toward Regio- and Diastereoselection

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posted on 18.09.2015, 00:00 by Yogesh P. Bharitkar, Mohua Das, Neha Kumari, M. Padma Kumari, Abhijit Hazra, Sagar S. Bhayye, Ramalingam Natarajan, Siddharth Shah, Sourav Chatterjee, Nirup B. Mondal
Curcumin has been transformed to racemic curcuminoids via an azomethine ylide cycloaddition reaction using isatin/acenaphthoquinone and proline as the reagents. The products were characterized by extensive 1D/2D NMR analysis and single-crystal X-ray crystallographic studies. The enantiomers of one racemic product were separated by HPLC on a Chiralcel OD-H column and were indeed confirmed by the CD spectra of the separated enantiomers.