Short Syntheses of (-)-( R )-Pyrrolam A and (1S)-1-Hydroxyindolizidin-3-one

Abstract

(-)-(R)-Pyrrolam A was prepared in five steps, 95% ee and 25% yield, from (R)-benzyl prolinate. Closure of the pyrrolidine ring was effected by a domino addition-Wittig alkenation reaction with ylide Ph₃PCCO, immobilized on a polystyrene resin. An indolizidinone was obtained likewise from (R)-benzyl pipecolate. The reduction of 1-ketopyrrolizidinones and 1-ketoindolizidinones is described.

Key words

domino reactions - solid-phase organic synthesis - indolizidines­ - pyrrolam A - heterocycles

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