Progress towards the pyrrolizidine alkaloid xenovenine (223H) via hydroamination.
| dc.contributor.advisor | Robinson, Ross Stuart. | |
| dc.contributor.author | Dralle, Lesley. | |
| dc.date.accessioned | 2016-10-04T10:52:56Z | |
| dc.date.available | 2016-10-04T10:52:56Z | |
| dc.date.created | 2016 | |
| dc.date.issued | 2016 | |
| dc.description | Master of Science in Chemistry. | en_US |
| dc.description.abstract | Many natural products, pharmaceuticals and fine chemicals possess carbon-nitrogen bonds and thus the formation of such bonds is of great importance. Pyrrolizidine, indolizidine, quinolizidine and lehmizidine alkaloid skeletons all contain C–N bonds and are potentially accessible via a general synthetic route utilising hydroamination. The synthesis of the biologically active nitrogen containing pyrrolizidine alkaloid xenovenine 4 isolated from Solenopsis cryptic thief ants and Dendrobates poison dart frogs was attempted. One of the key intermediates, ethyl 2-[(5R)-5-methyltetrahydro-2Hpyrrol- 2-ylidene]acetate 127, was successfully synthesised in 7 steps from (S)-pyroglutamic acid through a lactim ether intermediate. The pivotal ring forming ZnCl2 catalysed 5-exo-dig hydroamination was unfortunately not attempted after the failed C-propargylation of ethyl 2-[(5R)-5- methyltetrahydro-2H-pyrrol-2-ylidene]acetate 127. | en_US |
| dc.identifier.uri | http://hdl.handle.net/10413/13459 | |
| dc.language.iso | en_ZA | en_US |
| dc.subject | Pyrrolizidines. | en_US |
| dc.subject | Alkaloids. | en_US |
| dc.subject | Theses -- Chemistry. | en_US |
| dc.subject | Pyrrolizidine alkaloid xenovenine. | en_US |
| dc.subject | Hydroamination. | en_US |
| dc.title | Progress towards the pyrrolizidine alkaloid xenovenine (223H) via hydroamination. | en_US |
| dc.type | Thesis | en_US |