Pseudopelletierine is the main

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

derived from the root-bark of the

pomegranate The pomegranate (''Punica granatum'') is a fruit-bearing deciduous shrub in the family Lythraceae, subfamily Punicoideae, that grows between tall. The pomegranate was originally described throughout the Mediterranean Basin, Mediterranean re ...

tree (''

Punica granatum The pomegranate (''Punica granatum'') is a fruit-bearing deciduous shrub in the family Lythraceae, subfamily Punicoideae, that grows between tall. The pomegranate was originally described throughout the Mediterranean Basin, Mediterranean re ...

''), along with at least three other alkaloids: pelletierine, isopelletierine, and methylpelletierine (C9H17ON), which yield 1.8, 0.52, 0.01, and 0.20 grams per kilogram of raw bark. It is a

homolog In biology, homology is similarity due to shared ancestry between a pair of structures or genes in different taxa. A common example of homologous structures is the forelimbs of vertebrates, where the wings of bats and birds, the arms of prima ...

tropinone Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. It ...

, and can be synthesized in a manner analogous to the classical Robinson tropinone synthesis, using

glutaraldehyde Glutaraldehyde is an organic compound with the formula . The molecule consists of a five carbon chain doubly terminated with formyl (CHO) groups. It is usually used as a solution in water, and such solutions exists as a collection of hydrates, c ...

(rather than succinaldehyde), acetonedicarboxylic acid, and methylammonium chloride. It was the starting material for Willstätter's 10-step synthesis of

cyclooctatetraene 1,3,5,7-Cyclooctatetraene (COT) is an unsaturated derivative of cyclooctane, with the formula C8H8. It is also known as nnulene. This polyunsaturated hydrocarbon is a colorless to light yellow flammable liquid at room temperature. Because of ...

, which was achieved after oxidation and several Hoffman elimination steps.

References

Alkaloids Ketones Nitrogen heterocycles Heterocyclic compounds with 2 rings {{ketone-stub