ASYMMETRIC-SYNTHESIS .28. HYDROXYLATED BENZOQUINOLIZIDINE ANALOGS OF PODOPHYLLOTOXIN VIA THE CN(R,S) METHOD

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...

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Bibliographic Details
Published inTetrahedron Vol. 49; no. 19; pp. 3995 - 4006
Main Authors LIENARD, P, QUIRION, JC, HUSSON, HP
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 07.05.1993
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BENZOQUINOLIZIDINE
CN(R,S) METHOD, ALPHA-AMINONITRILE, ALPHA-AMINOETHER, STEREOCONTROLLED ALKYLATION OF IMINIUM ION
ENANTIOSPECIFIC SYNTHESIS
ASYMMETRIC SYNTHESIS
PODOPHYLLOTOXIN ANALOGS
ALKALOIDS
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Summary: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.
ISSN:0040-4020
DOI:10.1016/S0040-4020(01)89913-0