Synthesis of (−)-deoxynupharidine by allenic hydroxylamine cyclisation
(−)-Deoxynupharidine has been synthesised via an intermediate that can also be used for other Nuphar alkaloids. Significant steps include the optimised enzymatic resolution of an allenic alcohol, highly diastereoselective silver-catalysed cyclisation of an allenic hydroxylamine, selective cross-meta...
| Main Authors: | , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2015
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| Online Access: | https://hdl.handle.net/10356/103835 http://hdl.handle.net/10220/25855 |
| _version_ | 1826110985486729216 |
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| author | Bates, Roderick Wayland Lim, Chia Juan Collier, Steven J. Sukumaran, Joly |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Bates, Roderick Wayland Lim, Chia Juan Collier, Steven J. Sukumaran, Joly |
| author_sort | Bates, Roderick Wayland |
| collection | NTU |
| description | (−)-Deoxynupharidine has been synthesised via an intermediate that can also be used for other Nuphar alkaloids. Significant steps include the optimised enzymatic resolution of an allenic alcohol, highly diastereoselective silver-catalysed cyclisation of an allenic hydroxylamine, selective cross-metathesis, diastereoselective intramolecular reductive amination, and stereoelectronically controlled enolate alkylation. |
| first_indexed | 2024-10-01T02:43:11Z |
| format | Journal Article |
| id | ntu-10356/103835 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T02:43:11Z |
| publishDate | 2015 |
| record_format | dspace |
| spelling | ntu-10356/1038352020-03-07T12:37:20Z Synthesis of (−)-deoxynupharidine by allenic hydroxylamine cyclisation Bates, Roderick Wayland Lim, Chia Juan Collier, Steven J. Sukumaran, Joly School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry (−)-Deoxynupharidine has been synthesised via an intermediate that can also be used for other Nuphar alkaloids. Significant steps include the optimised enzymatic resolution of an allenic alcohol, highly diastereoselective silver-catalysed cyclisation of an allenic hydroxylamine, selective cross-metathesis, diastereoselective intramolecular reductive amination, and stereoelectronically controlled enolate alkylation. 2015-06-10T08:48:48Z 2019-12-06T21:21:18Z 2015-06-10T08:48:48Z 2019-12-06T21:21:18Z 2015 2015 Journal Article Bates, R. W., Lim, C. J., Collier, S. J., & Sukumaran, J. (2015). Synthesis of (−)-deoxynupharidine by allenic hydroxylamine cyclisation. Asian journal of organic chemistry, 4(7), 652-658. 2193-5807 https://hdl.handle.net/10356/103835 http://hdl.handle.net/10220/25855 10.1002/ajoc.201500094 en Asian journal of organic chemistry © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry Bates, Roderick Wayland Lim, Chia Juan Collier, Steven J. Sukumaran, Joly Synthesis of (−)-deoxynupharidine by allenic hydroxylamine cyclisation |
| title | Synthesis of (−)-deoxynupharidine by allenic hydroxylamine cyclisation |
| title_full | Synthesis of (−)-deoxynupharidine by allenic hydroxylamine cyclisation |
| title_fullStr | Synthesis of (−)-deoxynupharidine by allenic hydroxylamine cyclisation |
| title_full_unstemmed | Synthesis of (−)-deoxynupharidine by allenic hydroxylamine cyclisation |
| title_short | Synthesis of (−)-deoxynupharidine by allenic hydroxylamine cyclisation |
| title_sort | synthesis of deoxynupharidine by allenic hydroxylamine cyclisation |
| topic | DRNTU::Science::Chemistry::Organic chemistry |
| url | https://hdl.handle.net/10356/103835 http://hdl.handle.net/10220/25855 |
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