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Title: Studies on asymmetric approaches to (-)-cytisine and related molecules
Author: Bisset, Alexander A.
Awarding Body: University of Warwick
Current Institution: University of Warwick
Date of Award: 2013
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In this project, the asymmetric pressure and transfer hydrogenation of a number of substrates was carried out in attempt to asymmetrically form 5-substituted 6- membered saturated heterocycles, directly applicable to the asymmetric synthesis of (-)-cytisine and other related compounds. The hydrogenation of N-acylaminoacrylate- like enamide 1 was successful, resulting in the formation of 5- substituted glutarimide 218 in up to 94 % ee. Unfortunately, subsequent reduction resulted in epimerisation and loss of ee, preventing an asymmetric synthesis of (-)- cytisine precursor 5. The asymmetric reduction of pyridones 2 and 3 (featuring proximal coordinating groups) did not proceed with any enantioselectivity; however, the racemic reduction products were successfully utilised in novel syntheses of cytisine precursor 5 and bispiperidine 6 respectively. The ATH of pyridyl methyl ketone 4 with (R,R)-RutethTsDPEN, (R,R)-248 resulted in the formation of pyridyl alcohol 303 in 78-83 % ee. This compound was converted to diastereomers (D1)-7a and (D2)-7b which are derivates of a cytisine precursor and other therapeutic targets.
Supervisor: Not available Sponsor: AstraZeneca (Firm)
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry