Simple chiral pyrrolidines as such or as subunits present in several naturally occurring molecules pose a great deal of biological interest. Appropriate substituents on these five member nitrogen chiral motifs are crucial for the desired biological activity. Functionalized pyrrolidines are ideal choice as building blocks for total synthesis.The use of enantiopure natural products obtained from renewable resources is the most effective method for the synthesis of desired enantiopure molecules. The synthesis of functionalized pyrrolidine based natural products with four carbon frame work can be directly achieved by employing malic or tartaric acids. The (2S,3S) and (2S,3R)-tetrahydro-3- hydroxy-5-oxo-2, 3-furandicarboxylic acids have been demonstrated as effective substitute for malic and tartaric acids to rare 3-substituted and 3,4- disubstituted pyrrolidinediones , reserve for the preparation of drug candidates namely homoproline derived ranirestat, N-Methyl-N-{(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl}amine, for premafloxacin, (3S,4R)-4-[(1S)-1,2-dihydroxyethyl]pyrrolidin-3-ol an inhibitor of UDP-Galf transferase, Plakoridine A, a cytotoxic towards murine lymphoma L1210 cells, Brivaracetam used for antiepileptic drugs, and for other potential naturally occurring molecules and functional molecules, in large amounts. Subsequently, the chiral pryrrolidine has been converted to analogue of anti-tumor alkaloid, Crispine A. The Chiron approach towards the total synthesis of (+)-Crispine A (1 )(figure1) also will be presented.Acknowledgements are due to CSIR vide project No.02 (0101)/12/EMR-II dt.31-10-2012References:Ibnusaud et al. RSC Adv. 2012  , 2, 9257�9285Allin, M.S et al. J. Org. Chem. 2007  , 72, 8972-8975

Synthesis of enantiopure 3-substituted, 3, 4-disubstituted pyrrolidinediones and related isoquinoline alkaloid

247th National Meeting (2014)

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