Synthesis of thromboxane A2 analogues.

EVANS, Elizabeth Hannah. (1984). Synthesis of thromboxane A2 analogues. Doctoral, Sheffield Hallam University (United Kingdom)..

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Abstract

The aim of the project was to synthesize novel thromboxane A2 analogues which would be potential thromboxane A2 antagonists. Three thromboxane A2 analogues were synthesized, methyl 7-[-5-(3-hydroxy-1-(E)-octenyl)-2-methylbicyclo[3.3.1]non-2-en-9-yl]-[syn]-(+/-)-5-(Z)-heptenoate, methyl 7-[-5-(hydroxy-1-(E)-octenyl)-2,2-dimethylbicyclo[3.3.1]non-9-yl]-[syn]-(-+)-5-(Z)-heptenoate and methyl 7-[-5-(3-hydroxy-l-(E)-octenyl)-2,2-dimethylbicyclo[3.2.1]oct-8-yl]-[syn]-(-)-(Z)-heptenoate from a common functionalised bicycloalkane. During the synthesis of these functionalised bicycloalkanes several unexpected products were observed. These included the formation of methyl 5-methyl-6-oxa-7-oxobicyclo[3.2.2]-nonanecarboxylate during the sulphuric acid catalysed cyclisation of methyl 2-oxo-l-(3'-oxobutyl)cyclopentane-carboxylate which was contrary to the work of W G Dauben and J W McFarland and the formation of ethyl 4-methyl-bicyclo[4.4.0]dec-4,6-dienecarboxylate from the treatment of ethyl 1-(3'-methylbut-2'-ene)-2oxocyclohexanecarboxylate with stannic chloride. Another interesting rearrangement reaction was the formation of methyl 2-methine-5-oxohexanoate as well as methyl 4-oxo-3-(3'-oxobutyl)-3-tetrahydrothio-phenecarboxylate during the Michael reaction of methyl vinyl ketone with methyl 4-oxo-3-tetrahydrothiophene-carboxylate. Methyl 2-(2-methylbut-3'-en-2-yl)-3-oxo-tetrahydrothiophenecarboxylate was also an unexpected product from the alkylation of methyl 3-oxo-tetrahydrothio-phenecarboxylate with l-bromo-3-methylbut-2-ene.

Item Type: Thesis (Doctoral)
Additional Information: Thesis (Ph.D.)--Sheffield Hallam University (United Kingdom), 1984.
Research Institute, Centre or Group: Sheffield Hallam Doctoral Theses
Depositing User: EPrints Services
Date Deposited: 10 Apr 2018 17:19
Last Modified: 09 May 2018 17:04
URI: http://shura.shu.ac.uk/id/eprint/19630

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