Synthetic Studies on Gibberellins

Goudie, Alexander Crossan (1972) Synthetic Studies on Gibberellins. PhD thesis, University of Glasgow.

Abstract

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.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1972
• Depositing User: Enlighten Team
• Unique ID: glathesis:1972-78593
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 30 Jan 2020 15:09
• Last Modified: 30 Jan 2020 15:09
• URI: https://theses.gla.ac.uk/id/eprint/78593