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Title: Synthetic studies on gibberellins
Author: Goudie, Alexander Crossan
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 1972
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A stereospecific synthesis of 3-methoxy-6,16-dioxo-9betaH-gibb-A-triene has been achieved in good yield, starting from a Diels-Alder reaction of itaconic acid with methyl 5-(p-methoxyphenyl)-trans, trans-penta-2,4-dienoate, the major products from which violate the cis addition principle. An efficient stereospecific synthesis of the multifunctional gibberellin synthon 3-methoxy-16,16-ethylenedioxy-9betaH-gibb-A-triene-4,6beta-dicarboxylic acid from 3-methoxy-6,16-dioxo-9betaH-gibb-A-triene is described. Attempted elaboration of 3-methoxy-16,16-ethylenedioxy-9betaH-gibb-A-triene-4,6beta-dicarboxylic acid to methyl 4alpha-carboxyl-10alpha-hydroxy-4beta-methyl-3,16-dioxo-9betaH-gibbane-6beta-carboxylate 4alpha →10alpha lactone, prepared from a mixture of gibberellin A4 and A7 as a relay compound to gibberellin A4, has resulted in this synthesis of methyl 3-methoxy-4-methyl-16,16-ethylenedioxy-9betaH-gibb-A-triene-6beta-carboxylate. A partial solution, by spectroscopic methods, of the problem of assignment of C-9 stereochemistry in gibbanes has been devised.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available