The Library
Studies on asymmetric approaches to (-)-cytisine and related molecules
Tools
Bisset, Alexander A. (2013) Studies on asymmetric approaches to (-)-cytisine and related molecules. PhD thesis, University of Warwick.
|
Text
WRAP_THESIS_Bisset_2013.pdf - Submitted Version Download (14Mb) | Preview |
Official URL: http://webcat.warwick.ac.uk/record=b2692595~S1
Abstract
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.
Item Type: | Thesis (PhD) |
---|---|
Subjects: | Q Science > QD Chemistry |
Library of Congress Subject Headings (LCSH): | Asymmetric synthesis, Cytisine, Hydrogenation |
Official Date: | February 2013 |
Institution: | University of Warwick |
Theses Department: | Department of Chemistry |
Thesis Type: | PhD |
Publication Status: | Unpublished |
Supervisor(s)/Advisor: | Wills, Martin |
Sponsors: | AstraZeneca (Firm) |
Extent: | 288 leaves : illustrations. |
Language: | eng |
Request changes or add full text files to a record
Repository staff actions (login required)
View Item |
Downloads
Downloads per month over past year