Flindersia ifflaiana

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 alkaloids from Ravenia spectabilis and Flindersia ifflaiana exhibit an interesting structural variation within the quinoline group and some evidence has been presented for their genesis via biological Claisen rearrangements. ... 

Lemobiline (113) (137), also isolated from Flindersia ifflaiana E. Muell. (138), was obtained along with (— )-ravenoline (114) and arborin-ine. When (— )-ravenoline is treated with 48% hydrobromic acid or with hydrogen chloride in acetic acid at room temperature it generates (— )-lemobihne in 65% yield (139). 

C. Alkaloids of Flindersia ifflaiana F. Muell and Ravenia spectabilis Engl. 171... 

In order to compare synthetic ifflaiamine with the natural alkaloid, Chamberlain and Grundon (198, 199) reexamined a crude alkaloid extract derived from the wood of Flindersia ifflaiana and obtained two isomeric alkaloids. Ifflaiamine (264) mp 122-125° [a]D-6.2° in methanol and -9.15° in chloroform picrate, mp 189-192° had properties different from those reported earlier (Volume IX). The second alkaloid (mp 53-54° picrate, mp 188-191°) was shown to be the 1,2-dimethylallyl derivative 267 by comparison with the synthetic racemate (mp 106-108° picrate, mp 186-190°). The alkaloid was levorotatory, but too little was available to obtain an accurate value of the specific rotation. 

Ifflaiamine II l,2, 3, 3 -tetraMe Flindersia ifflaiana [42] Lunasia amara [50]... 

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