Synthesis, structure and stereochemistry of quinoline alkaloids from Choisya ternata.
A range of seventeen quinoline alkaloids, involving several types of oxidations during their biosynthetic pathways, have been isolated from leaves of Choisya ternata. In addition to the nine known quinoline alkaloids, eight new members of the furoquinoline family, derived mainly from prenylation at C-5 (including two novel hydroperoxides), have been identified. The absolute configurations and enantiopurity values of all chiral quinoline alkaloids have been determined. One of the isolated alkaloids, 7-isopentenyloxy-gamma-fagarine, has been used as a precursor for the chemical asymmetric synthesis of the enantiopure alkaloids: evoxine, anhydroevoxine and evodine. The possible roles of oxygenase and other oxygen-atom-transfer enzymes, in the biosynthetic pathways of the C. ternata alkaloids, have been discussed.
Boyd
Derek R
DR
School of Chemistry and Chemical Engineering, The Queen's University of Belfast, Belfast, UK.
Sharma
Narain D
ND
Loke
Pui L
PL
Malone
John F
JF
McRoberts
W Colin
WC
Hamilton
John T G
JT
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D027821:Rutaceae / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
D000470:Alkaloids