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Structural and synthetic studies of some pyrrolidine, tropane and bisbenzylisoquinoline alkaloids

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Leow, Huck Meng (1979) Structural and synthetic studies of some pyrrolidine, tropane and bisbenzylisoquinoline alkaloids. PhD thesis, University of Tasmania.

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Abstract

A detailed phytochemical examination of the alkaloid content of
four species of the family Proteaceae - Bellendena montana, Darlingia
darlingiana, Darlingia ferruginea and Agastachys odorata - has been
undertaken.
A new group of pyrrolidine bases with a side-chain of varying
length terminating in a phenyl group has been isolated from D.
darlingiana. Spectroscopic and chemical evidence for the structures
of five new C17 and three new C15 pyrrolidine bases are presented.
The structural assignments were confirmed by syntheses, and in one
case, by X-ray crystallography, which also established the absolute
stereochemistry.
Four new minor alkaloids of the pyranotropane-type have been
isolated, three from B. montana and one from D. darlingiana. Four
previously described pyranotropane alkaloids were reisolated from
the Bellendena and Darlingia species; the presence of eight alkaloids
of the tropane-type in the four species, including a unique tropene of
biosynthetic interest in A. odorata, was also confirmed.
Two of the tropane alkaloids have been synthesised and their
absolute stereochemistries established. Progress towards the synthesis
of a third tropane alkaloid is reported.
Four unknown bases were also isolated from B. montana; evidence
is presented to support a tentative trilactone structure proposed for
one of these.
Some general observations on the proteaceous alkaloids are made
and a possible mode of biosynthesis of these alkaloids is suggested.
Two species of the family Monimiaceae, Daphnandra johnsonii and Nemuaron vieillardii, were investigated.
An examination of the alkaloid content of the rare new species,
D. johnsonii, has supported its taxonomic classification as a distinct
species. Three new bisbenzylisoquinoline alkaloids were isolated;
one of these is unique amongst the biscoclaurine alkaloids of the
head-to-head type in having a C6-hydroxyl group; the other two
belong to the dibenzodioxin type of biscoclaurine alkaloids. Four
known alkaloids which occur in other Daphnandra spp. were also
isolated.
A new bisbenzylisoquinoline alkaloid with a C5-C6' ether linkage
has been isolated from N. vieillardii.
Spectroscopic and chemical evidence for the structures of the
new alkaloids are presented.
The thesis is divided into three parts. The pyrrolidine
alkaloids are discussed in Part I, the tropane alkaloids in Part II,
and the bisbenzylisoquinoline alkaloids in Part III.

Item Type: Thesis (PhD)
Keywords: Botanical chemistry, Proteaceae, Alkaloids
Copyright Holders: The Author
Copyright Information:

Copyright 1979 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, 1979. Includes bibliographical references

Date Deposited: 19 Dec 2014 02:22
Last Modified: 14 Jul 2017 01:23
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