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Title: Synthetic studies on gibberellins
Author: Orr, Alexander Ferguson
ISNI:       0000 0001 3459 8352
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 1974
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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.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available