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Title: Towards the total synthesis of the herqulines
Author: Hart, Jennifer Marian
Awarding Body: University of Leeds
Current Institution: University of Leeds
Date of Award: 2004
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Herqulines A and B (1 and 2 respectively) were isolated from the culture broth of a soilderived Penicillium species in 1979 and 1996 respectively. They were both found to inhibit platelet aggregation, with herquline B (whose stereochemistry has not been elucidated) being the stronger inhibitor. The herqulines are thought to be biosynthesised from tyrosine 3, but very little work relating to their total synthesis has been reported. This thesis describes work towards the total synthesis of herqulines A and B, focussing on two key reactions: the linking of two tyrosine molecules via the aromatic rings, and the reduction of the aromatic rings to give the required pattern of unsaturation. However, aryl-aryl bond formation followed by the symmetrical reduction of the biphenyl system was not successful- the required regiochemistry of the reduction posed a particular problem. Although the target molecules 1 and 2 were not generated, strategies for their total synthesis were investigated. The most recently examined approach, which avoided the regiochemical problem mentioned above and involved the reduction of the aromatic ring of tyrosine followed by the linking of two reduced tyrosine moieties, appears promising.
Supervisor: Johnson, P. Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available