Hyperaspine alkaloid

Hyperaspine alkaloid (1) was isolated from ladybird beetle Hyperaspis campestris. 

Hyperaspine (1), a perhydropyrido[l,2-c][l,3]oxazine alkaloid was isolated from the ladybird beetle H. campestris (01TL4621). 9-Epi-6-epipinidinol (90), a piperidine alkaloid, was prepared from a perhydropyrido[l,2-c][l,3]oxazin-l-one derivative (98T13505). Perhydropyrido[l,2-c][l,3]oxa-zin-l-ones were used to prepare 2,6-disubstituted piperidines (96CJC2434). 

Hyperaspine (23) is the first 3-oxaquinolizidine alkaloid reported so far from ladybird beetles. Its skeleton, however, which is based on a chain of 13 carbon atoms, is biosynthetically related to those of the homotropane and perhydroazaphenalene alkaloid already isolated from ladybirds [38]. 

Figure 9.9 Some alkaloids with bridge-head nitrogen and a diamine from ladybirds. The biosynthetic scheme for hyperaspine is the author s present suggestion only. No scheme for the formation of the azanaphthacene part is offered...

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