Flindersia species

Ritchie E 1964 Chemistry of Flindersia species. Rev Pure Appl Chem 14 47-57... 

Breen G J W, Ritchie E, Taylor W C 1962 The chemical constituents of Australian Flindersia species. XVI. The constituents of the wood of Flindersia laevicarpa C. T. White Francis. Austr J Chem 15 819-823... 

Pyranoquinolines (Phe pyridine C50) include the antimicrobials flindersine and jV -methylflindersine from Flindersia and Glycosmis species (Rutaceae). 

Several further species of Flindersia have been examined for alkaloids and other extractives and the chemistry of this genus has been reviewed (118). The only new alkaloid found was iflflaiamine ([a] n — 0.6° hydrate, mp 62°-63° picrate, mp 207°-209°), the sole alkaloid of the wood of Flindersia ifflaiana F. Muell. (119), which is a dihydrofuroquinoline (XX). Its structure was largely elucidated by spectroscopic measurements. Its UV- and IR-spectra showed it to be a 2-alkoxy-4-quinolone, and the NMR-spectrum showed the presence of three C-methyl groups and one A-methyl (attached to aromatic ring N), a 1,2-disubstituted benzene ring, and other evidence supporting the 2-alkoxy-4-quinolone structure. 

The occurrence of (1,1-dimethylallyl)- and (l,2-dimethylallyl)quinoline derivatives in Flindersia and Ravenia species and the isolation of the prenyl ether 261 from Ravenia (Section V,B) suggested that the biosynthesis of this group of alkaloids might proceed via Claisen and abnormal Claisen rearrangements as in the synthetic route (Scheme 22, Section V, B). 

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