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Title: Studies towards the synthesis of the antibiotic lactonamycin
Author: Walsh, Lee
ISNI:       0000 0004 5348 9540
Awarding Body: Imperial College London
Current Institution: Imperial College London
Date of Award: 2014
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Transition metal-free, thermal cyclisation methodology has been demonstrated previously in the Parsons group, with the vision of applying the process to a novel synthesis of the antibiotic Lactonamycin. i. The synthesis of the aglycone of i has been proposed from the pentacyclic intermediate ii, which itself is the hypothesised product of the Parsons-BoardWaters cyclisation of the ene-diyne iii. (Scheme A - see thesis abstract) The phthalide v was synthesised from 2,5-dimethoxybenzaldehyde in 3 steps in moderate yield and was seen as a common starting material for the subsequent routes devised to provide the key aldehyde vi. A further mode of complexity was proposed by attempting to perform the Claisen rearrangement of the alkene vii in cascade with the aforementioned cyclisation to give the amide ii. (Scheme B - see thesis abstract)
Supervisor: Parsons, Philip Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available