1-Methyl�(2S)�acetyl methyl pyrrolidin-5-ones were prepared from (3R)-aziridin-2-yl-propanoate through N-methylative aziridine ring opening reaction with cyanide nucleophile followed by reductive cyclization. Methylation and the subsequent selective reductions afforded the asymmetric synthesis of (- )-hygroline and (- )-pseudohygroline which are pyrrolidine alkaloid natural products isolated from Carallia brachiata with potent biological and pharmacological activities.

Asymmetric synthesis of (-)-hygroline and (-)-pseudohygroline from chiral aziridine-2-carboxylate

248th National Meeting (2014)

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