The resins of the North Queensland Kauri pines and related diterpene chemistry.

Marty, Robert Arthur (1969). The resins of the North Queensland Kauri pines and related diterpene chemistry. PhD Thesis, School of Molecular & Microbial Sciences, The University of Queensland.

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Author Marty, Robert Arthur
Thesis Title The resins of the North Queensland Kauri pines and related diterpene chemistry.
School, Centre or Institute School of Molecular & Microbial Sciences
Institution The University of Queensland
Publication date 1969
Thesis type PhD Thesis
Supervisor R.M. Carman
Total pages 134
Collection year 2005
Language eng
Subjects L
06 Biological Sciences
Formatted abstract

Gas chromatography of methylated resins has shown that there are three chemically distinct species of Kauri Pine in Australia. One of these species (A. robusta) is found in South Queensland, while all three grow in North Queensland. These results are in accord with the views of some foresters and botantists. The North Queensland species are called A. palmers tonti (chemically identical with A. robusta), Bull Kauri and Black Kauri.

Bull and Black Kauri Pine have both been shown to exude the known resin acids cis- and trans-communic (8C and 6B), sandaracopimaric (AP), abietic (5Q), and neoabietic (17Q) acids, and the new natural product C^-monomethyl agathate (13A). As well as these compounds Bull Kauri resin contains the two new naturally-occurring diterpenoids 15-hydroxyabietic and 15-hydroxydehydroabietic acids (isolated as their methyl esters (48R) and (49R)), while Black Kauri exudes agathalic (25A) and acetoxy agatholic (24A) acids as well as the known agatholic acid (12A).

Further to the work of Cowley on the polymeric fraction of A . robusta resin, it has been shown by chemical and spectroscopic evidence that the polymers from A. robusta and Bull Kauri resins are formed principally by 3,4 polymerization of communio acid (6B). Initial investigations of Black Kauri polymer indicates. that it is predominantlya co-polymer of C16 -monomethyl agathate (13A) and communic acid (6B) -- the two major monomeric components of the resin.

The syntheses from agathic acid (1A) of two new series of "abnormal" diterpene acids and esters -- ▲8,9 isomers of agathic acid type molecules and the epimers of abietic acid type molecules -- have been carried out. It has been demonstrated by gas-liquid chromatography that these compounds do not occur in detectable amounts in Kauri resins and that the two North Queensland Kauri Pines produce only "normal" compounds. The 4-epiabietates have been converted to methyl callitrisate (methyl 4-epidehydroabietate) (71R) providing an unambiguous proof of the absolute stereochemistry of this latter compound. 

The optical rotations of compounds with basic structure F have been investigated, and in all cases studied the anomalous literature values have been shown to be incorrect. These findings necessitated the repetition of some of the original work on the structure of communio acid (6B), the absolute stereochemistry of which was determined through molecules of type F. Despite the erroneous optical rotations of (37F), (81F), and (86F) the original assignment of stereochemistry was found correct.

Keyword Agathis

Document type: Thesis
Collection: UQ Theses (RHD) - UQ staff and students only
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Created: Fri, 13 Nov 2015, 10:48:48 EST by Ms Christine Heslehurst on behalf of Research Management Office