Eupomatia

Aporphine alkaloids have been identified in Eupomatia laurina, which also gave a positive test in this study. 

The biogenetic relevance of spirodienone intermediate A is supported by the isolation of other spirodienones from Eupomatia laurina, namely the eupodienones [85], which were found to rearrange under acid conditions to give dibenzocyclooctadiene-type lignans [86]. 

The 1,6-diazafluoranthene eupolauridine (69) is also found in Cananga odorata Hook f. et Thompson (Annonaceae).73 Eupomatia laurina R. Br., which was the... 

Stephania japonica Liriodendron tulipifera Triclisia patens Liriodendron tulipifera Eupomatia laurina Cananga odorata Talauma mexicana ... 

An investigation of the alkaloidal content of the Australian Eupomatia laurina R. Br. (Eupomatiaceae), yielded a number of alkaloids, among which are the oxoaporphine liriodenine and the 7-hydroxynoraporphine norushinsunine. A new minor alkaloid from this source is eupolauridine (48) whose structure was proven conclusively by total synthesis (Scheme 6). ... 

Analogous rearrangements were reported for similar systems such as proaporphines , the alkaloids of Croton sparsiflorusMorong and cannabinoids . The dienone-phenol and dienol-benzene rearrangements were studied in the eupodienone-1 series (a constituent of Eupomatia laurina R. Br.). These compounds 311 were transformed under a variety of acidic conditions into dibenzocyclooctene derivatives (equation 149). 

Another monogeneric family of great antiquity, the Eupomatiaceae, was also investigated in the University of Sydney, and the first species studied, Eupomatia laurina. 

In 1978, Taylor et al. isolated a yellow crystalline substance, EL-base-5, from the bark of Eupomatia laurina (Eupomatiaceae) R. Br. collected in North Queensland 183). A more thorough investigation of this material in 1991 revealed that it consisted of two closely related compounds, eupomatidine-2 (431) and eupomatidine-3 (432). Their structure elucidations were reported, along with that of the newly isolated alkaloid eupomati-dine-1 (430), from the aerial parts of E. bennettii collected in the Mt. Lindsay Forest, New South Wales (iS4). 

An important example is the formal synthesis of eupolauramine, an alkaloid from the bark of the African plant Eupomatia laurina. This approach involves addition of the carbanion of allyl phenyl sulfone to l-methoxy-4-nitronaphthalene followed by cOTiversion of the o adduct formed into the conesponding nitrosoarene. Further intramolecular condensation affords phenylsulfonyl-substituted azaphenanthrene (Scheme 83) [82]. The sulfone obtained was transformed into tricyclic azaaromatic acid, from which in turn the final alkaloid can be obtained following the known procedure [206],... 

Azafluoranthene and Tropoloisoquinoline Alkaloids Aporphine Alkaloids Biogenesis Biological Activity Aristolactams and Aristolochic Acid Eupomatia Alkaloids Proaporphine Alkaloids... 

This small group of alkaloids is only known from the genus Eupomatia (Eupomatiaceae). These compounds appear to be derived from oxoaporphine alkaloids, although little experimental work has been done to establish this proposal (Fig. 32.16) (Taylor, 1985). 

Fig. 32.16. Eupomatia alkaloids (modified from Taylor, 1985 used with permission of the copyright owner. Academic Press, Orlando, FL).

Myristicaceae Magnolioideae Liriodendron Galbulimima Degeneria Eupomatia... 

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