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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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Abstract

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)
Keywords: Alkaloids, Proteaceae
Copyright Holders: The Author
Copyright Information:

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
would be pleased to hear from the copyright owner(s).

Additional Information:

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

Date Deposited: 08 Dec 2014 23:53
Last Modified: 16 Sep 2016 04:47
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