NOVEL SYNTHESIS OF THE INDOLIZIDINE ALKALOID SKELETON WITH APPROPRIATE FUNCTIONALITY AND STEREOCHEMISTRY FOR USE AS A 'CHIRAL SCAFFOLD'

A stereocontrolled synthesis of the indolizidine alkaloid skeleton has been achieved via an intramolecular, photoinduced reaction of (5S)-5-triisopropylsilyloxymethyl-3-{2′ -[(3″S)-3″ -methoxypyrrolidinyl]ethyl}furan-2-(5H)-one, which can be obtained in a highly convergent fashion from (5S)-5-triisopropylsilyloxymethyltetrahydrofuran-2-one and (3S)-3-methoxypyrrolidine.