Synthesis of piperidine natural products by allenic cyclisation
The various strategies for the synthesis of Nuphar alkaloids that have been reported to date are reviewed. Earlier applications of silver catalysed cyclisation of allenic hydroxylamines are discussed. The synthesis of four Nuphar alkaloids using allenic hydroxylamine cyclisation is discussed. The al...
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sg-ntu-dr.10356-550662023-02-28T23:47:52Z Synthesis of piperidine natural products by allenic cyclisation Lim, Chia Juan Roderick Wayland Bates School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis The various strategies for the synthesis of Nuphar alkaloids that have been reported to date are reviewed. Earlier applications of silver catalysed cyclisation of allenic hydroxylamines are discussed. The synthesis of four Nuphar alkaloids using allenic hydroxylamine cyclisation is discussed. The allenic alcohol precursor is obtained in optically active form using an enzymatic resolution procedure, optimised by DOE methods. The cyclisation reaction is found to be highly dependant on the specific silver salt employed and also on the presence of moisture. The side chains required for the unnamed Nuphar indolizidine and Nupharamine are introduced by cross metathesis. The side chain for (-)-deoxynupharidine and Castoramine are introduced by cross metathesis, followed by a subsequent stereoselective alkylation. The previous synthesis of Cernuine is discussed. Prelimary studies for the formation of 1,3-diamines via N-N tethered allenic cyclisation or Michael addition are discussed. A potential precursor for the preparation of the 1,3-diamine moiety in the total synthesis of Cernuine using Denmark’s carbonylation and Feringa’s methylation is described. DOCTOR OF PHILOSOPHY (SPMS) 2013-12-11T08:08:15Z 2013-12-11T08:08:15Z 2013 2013 Thesis Lim, C. J. (2013). Synthesis of piperidine natural products by allenic cyclisation. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/55066 10.32657/10356/55066 en 221 p. application/pdf |
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DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis Lim, Chia Juan Synthesis of piperidine natural products by allenic cyclisation |
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The various strategies for the synthesis of Nuphar alkaloids that have been reported to date are reviewed. Earlier applications of silver catalysed cyclisation of allenic hydroxylamines are discussed. The synthesis of four Nuphar alkaloids using allenic hydroxylamine cyclisation is discussed. The allenic alcohol precursor is obtained in optically active form using an enzymatic resolution procedure, optimised by DOE methods. The cyclisation reaction is found to be highly dependant on the specific silver salt employed and also on the presence of moisture. The side chains required for the unnamed Nuphar indolizidine and Nupharamine are introduced by cross metathesis. The side chain for (-)-deoxynupharidine and Castoramine are introduced by cross metathesis, followed by a subsequent stereoselective alkylation. The previous synthesis of Cernuine is discussed. Prelimary studies for the formation of 1,3-diamines via N-N tethered allenic cyclisation or Michael addition are discussed. A potential precursor for the preparation of the 1,3-diamine moiety in the total synthesis of Cernuine using Denmark’s carbonylation and Feringa’s methylation is described. |
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Roderick Wayland Bates |
author_facet |
Roderick Wayland Bates Lim, Chia Juan |
format |
Theses and Dissertations |
author |
Lim, Chia Juan |
author_sort |
Lim, Chia Juan |
title |
Synthesis of piperidine natural products by allenic cyclisation |
title_short |
Synthesis of piperidine natural products by allenic cyclisation |
title_full |
Synthesis of piperidine natural products by allenic cyclisation |
title_fullStr |
Synthesis of piperidine natural products by allenic cyclisation |
title_full_unstemmed |
Synthesis of piperidine natural products by allenic cyclisation |
title_sort |
synthesis of piperidine natural products by allenic cyclisation |
publishDate |
2013 |
url |
https://hdl.handle.net/10356/55066 |
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1759856018238472192 |