Asymmetric synthesis XXVIII: Hydroxylated benzoquinolizidine analogues of podophyllotoxin via the CN(R,S) method

DOI: 10.1016/S0040-4020(01)89913-0

Source and publish data:

Tetrahedron p. 3995 - 4006 (1993)

Update date:2022-08-04

Topics:

Authors:

Lienard Lienard

Quirion Quirion

Husson Husson

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Article abstract of DOI:10.1016/S0040-4020(01)89913-0

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.

Full text of DOI:10.1016/S0040-4020(01)89913-0

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Product name:(3R,5S,8aR)-5-((R)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile

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