Synthetic Studies in the Gibberellic Acid Field

Money, Thomas (1960) Synthetic Studies in the Gibberellic Acid Field. PhD thesis, University of Glasgow.

Abstract

A. The structural, stereochemical and biogenetic studies on gibberellic acid and the gibberellins are reviewed. An account of the synthetic approaches to the degradation products of gibberellic acid is also provided. B. Various synthetic routes to gibberone, a degradation product of gibberellic acid, have been investigated. The main synthetic approach, which involved the preparation of suitably oriented spiro-compounds from 4-methylindan-1-one, provided us with a tricyclic intermediate which is theoretically capable of elaboration to gibberone. An attempted cyclisation of this intermediate provided us with a product which possessed physical properties similar to 6-oxo-gibberone. The exact nature of this product awaits elucidation. An attempt to prepare the ozonolysis product of gibberone is also described. C. Synthetic approaches to gibberic acid, an acid-catalysed rearrangement product of gibberellic acid, have been explored. These involved the initial preparation of either a suitably substituted coumarin or indanone. Attempts to convert these compounds to a suitable tricyclic intermediate are described. Promising results have been obtained from investigations concerning a route to gibberic acid which involves the use of spiro-type compounds. The latter route is essentially similar to that used for gibberone.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1960
• Depositing User: Enlighten Team
• Unique ID: glathesis:1960-79394
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 05 Mar 2020 10:16
• Last Modified: 05 Mar 2020 10:16
• URI: https://theses.gla.ac.uk/id/eprint/79394