Tetrahedron p. 3995 - 4006 (1993)
Update date:2022-08-04
Topics:
Lienard
Quirion
Husson
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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