Complementary chemoenzymatic routes to both enantiomers of febrifugine

Two complementary strategies for the synthesis of febrifugine are detailed based on previously developed chemoenzymatic approaches to the 3-hydroxypiperidine skeleton. The introduction of the quinazolone-containing side chain in both strategies was based on an N-acyliminium ion-mediated coupling rea...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2009-01, Vol.7 (14), p.2976-2980
Main Authors: Wijdeven, Marloes A, van den Berg, Rutger J F, Wijtmans, Roel, Botman, Peter N M, Blaauw, Richard H, Schoemaker, Hans E, van Delft, Floris L, Rutjes, Floris P J T
Format: Article
Language:English
Subjects:
Catalysis
Piperidines - chemical synthesis
Piperidines - chemistry
Quinazolines - chemical synthesis
Quinazolines - chemistry
Stereoisomerism
Substrate Specificity
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Summary:Two complementary strategies for the synthesis of febrifugine are detailed based on previously developed chemoenzymatic approaches to the 3-hydroxypiperidine skeleton. The introduction of the quinazolone-containing side chain in both strategies was based on an N-acyliminium ion-mediated coupling reaction.
ISSN:1477-0520
1477-0539
DOI:10.1039/b901670h