Abstract

The condensation of 2-cyano-6-phenyloxazolopiperidine synthon (−)- 5 with piperonal, gave after reduction, the optically pure pivotal amino-alcohol 8 . Two strategies were developed to prepare the epimeric azapodophyllotoxin analogues 2 and 3 via Grignard reactions on an iminium ion generated from the common intermediate 8 . The first strategy was based on an intramolecular reaction while the second involved a stereocontrolled addition reaction on iminium ion 20 .

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