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Structural and synthetic studies of alkaloids of the Proteaceae


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Gillard, John Walter 1975 , 'Structural and synthetic studies of alkaloids of the Proteaceae', PhD thesis, University of Tasmania.

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Following the discovery of the presence of alkaloids in an endemic
Tasmanian Proteaceous species, Bellendena montana R.BR., a detailed
phytochemical examination for alkaloids has been undertaken. In
addition, three other species of the Proteaceae, Darlingia darlingiana
(F. MUELL) L.A.S. JOHNSON, Darlingia ferruginea, J.F. BAILEY, and
Agastachys odorata R.BR., also found to contain alkaloids, have been
subjected to a similar examination.
This study has resulted in the isolation of fifteen alkaloids,
of which twelve have been structurally identified by spectroscopy and
synthesis. The structures of the bases have been shown to be
derivatives of the tropane class; eight alkaloids with novel structures
have been classified in two new tropane categories, those of
y-pyronotropanes and 2-benzoyl tropanes. Use has been made of proton
magnetic resonance and carbon magnetic resonance spectroscopy in
determining relative stereochemistries of the bases, and a discussion
of the 13C N.M.R. of y-pyrones is given. Two stereochemical series
of tropane diol esters have been prepared and the spectroscopic data
relating to these bases are presented.
A general synthetic procedure has been developed to apply to the
y-pyronotropanes; each of the naturally occurring alkaloids has been
synthesized by a condensation between tropan-3-one and an enol
ether derivative of a β-keto acid chloride.
The probable biogenetic relationships between the alkaloids of the
species under study and those recently described, of Knightia deplanchei
VIEILL. ex BROGN et GRIS (Proteaceae) are described in terms of a
biosynthesis from ornithine and a polyketide chain terminated with a
non-acetate moiety.

Item Type: Thesis - PhD
Authors/Creators:Gillard, John Walter
Keywords: Alkaloids, Proteaceae
Copyright Holders: The Author
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Copyright 1975 the Author - The University is continuing to endeavour to trace the copyright
owner(s) and in the meantime this item has been reproduced here in good faith. We
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Additional Information:

Thesis (Ph.D.) - University of Tasmania, 1976. Includes bibliographical references

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