Abstract:
The first part of this thesis is concerned with the structure, stereochemitry, and reactions of asperuloside, a labile glucoside widely distributed
among plants of the family Rubiaceae. Its interest to this Departmen arose
from its abundant, occurrence in Coprosma species, most of which are native to
New Zealand. Since the aglycone of asperuloside is now known to possess the
carbon skeleton (1) , asperuloside may be formally regarded as monoterpenoid.
This Introduction therefore considers the structures, interrelationships, and
biogenesis of cyclopentanoid monoterpenoids possessing the 1,2-dimethyl-3-isopropylcyc clopentane carbon skeleton (1).
Cyclopentanoid Monoterpenoids:
Although acyclic and cyclohexanoid monoterpenoids have been characterised
for nearly eight years, naturally occurring compounds possessing the carbon
skeleton (1) have been defined relatively recently. Despite their frequently
unusual chemical behaviour and physiological actions, which have often been
recorded in the early literature, progress in the elucidation of their structures
has awaited the application of modern physical techniques. The carbon skeletons
are frequently highly oxygenated, and the characteristic chemistry of the compounds
arises from the interactions of contiguous functional groups. Since the
chemistry of the type compounds, nepetalactone (2), iridomyrmecin (3), and iridodial
(4) has been reviewed, only more recent work will be discusse below.
