Synthetic Studies on Gibberellins

Daoud, Khalid Mahmood (1978) Synthetic Studies on Gibberellins. PhD thesis, University of Glasgow.

Abstract

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.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1978
• Depositing User: Enlighten Team
• Unique ID: glathesis:1978-78795
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 30 Jan 2020 14:54
• Last Modified: 30 Jan 2020 14:54
• URI: https://theses.gla.ac.uk/id/eprint/78795