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 reaction.
Wijdeven
Marloes A
MA
Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, NL-6525 AJ Nijmegen, The Netherlands.
van den Berg
Rutger J F
RJ
Wijtmans
Roel
R
Botman
Peter N M
PN
Blaauw
Richard H
RH
Schoemaker
Hans E
HE
van Delft
Floris L
FL
Rutjes
Floris P J T
FP
D002384:Catalysis; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D010880:Piperidines; D011799:Quinazolines; C001207:febrifugine