Use this URL to cite or link to this record in EThOS:
Title: Synthetic studies on gibberellins
Author: Daoud, Khalid Mahmood
ISNI:       0000 0001 3404 4819
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 1978
Availability of Full Text:
Access from EThOS:
Access from Institution:
As part of a programme directed towards the total synthesis of the plant hormones - the gibberellins - efficient synthesis of 4-carboxy-5,6-dimethoxyindanone and related compounds were required. This thesis describes the synthesis of 4-4-carboxy-5,6-dimethoxyindanone and related compounds from methyl beta-(2-hydroxymethyl-3-hydroxy-4-methoxy-phenyl)propionate which was derived from isovanillin using a regiospecific benzeneboronic acid catalysed hydroxymethylation reaction. The same indanone was synthesised by an independent route from opianic acid, a degradation product of the alkaloid narcotine. 4-Methyl-5-hydroxy-6-methoxyindanone and related compounds v/ere synthesised in a related fashion from isovanillin. An efficient route to a monoprotected derivative of 4-methylindane-5,6-quinone-3-oxo-4,4-oxoethylenedioxy-5-methylbicyclo[4.3.0]nona-1,5-diene is described together with its facile Diels-Alder reaction with methyl vinyl ketone. The stability of the phenylboronate derivative of an ortho-hydroxybenzyl alcohol towards polyphosphoric acid cyclisation conditions is also recorded.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available