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Title: A convergent approach to produce the basic skeleton of the marine natural product eleutherobin and analogues
Author: Tirnaveanu, A. E.
Awarding Body: Queens University Belfast
Current Institution: Queen's University Belfast
Date of Award: 2008
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Abstract:
Eleutherobin 1 was isolated in 1994 from the soft coral ofthe Elelltherobia species in Western Australia. E1eutherobin attracted interest as it showed in vitro cytotoxicity towards selected cancer cell lines. Due to the scarce availability of this exciting compound we proposed a convergent synthesis of eleutherobin believing that it would provide the necessary intermediates to scale up the production ofthis drug and analogues in order for the therapeutic activity to be investigated. In this project the formation of the basic skeleton of eleutherobin 1 was attempted, and the basic skeletons of two of its analogues (2 and 23). Molecules 1 and 2 are both diterpene glycosides, characterised by a fused tricyclic skeleton comprising six-, nine- and five membered rings, which are termed A, Band C respectively, with the difference in the substitution of C-4 position of ring C (1, R=' OMe, while 2, R= Me). Molecule 23 has the same structure as 2 with the difference that ring B has 10 carbon atoms. The formation of the so called 'northern' and 'southern' bonds of the basic skeleton of 1, 2 and 23 respectively remains at the basis of our convergent approach to the synthesis of eleutherobin 1 and its analogues 2 and 23. The identified key intermediates were successfully synthesised from the commercially available R-(-)-phellandrene and 2-methylfuran or 2,5-dimethylfuran respectively.
Supervisor: Not available Sponsor: Not available
Qualification Name: Queens University Belfast, 2008 Qualification Level: Doctoral
EThOS ID: uk.bl.ethos.492480  DOI: Not available
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