Synthetic Studies on Gibberellins

Orr, Alexander Ferguson (1974) Synthetic Studies on Gibberellins. PhD thesis, University of Glasgow.

Abstract

This thesis describes the investigation of two possible synthetic routes to 3-methoxy-6alpha-carbomethoxy-16-oxogibb-A-triene (I), an intermediate of potential significance in the synthesis of the plant hormone gibberellin A4. The first synthetic route required the preparation of a substituted indanone which was eventually achieved via a hydrofluorenone intermediate. Elaboration of this indanone to 3-methoxy-6alpha-carbomethoxy-I2,I6-dioxogibb-I,3,5(10),9-tetraene was accomplished, but the final step in this approach, hydrogenation of the latter compound to give the required keto-ester (I), could be effected only in low yield. In the course of this investigation a novel one-step conversion of a cyclohexene oxide to a trans 7,9-dioxabicyclo(4.3.0)nonane was effected. The second synthetic approach to the intermediate (I) involved elaboration of a bicyclo(3.2.1)octanone, but lack of time did not permit the more detailed study which this approach required.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: Organic chemistry
• Date of Award: 1974
• Depositing User: Enlighten Team
• Unique ID: glathesis:1974-78670
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 30 Jan 2020 15:04
• Last Modified: 30 Jan 2020 15:04
• URI: https://theses.gla.ac.uk/id/eprint/78670