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...

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Main Authors:	Bates, Roderick Wayland, Lim, Chia Juan, Collier, Steven J., Sukumaran, Joly
Other Authors:	School of Physical and Mathematical Sciences
Format:	Article
Language:	English
Published:	2015
Subjects:	DRNTU::Science::Chemistry::Organic chemistry
Online Access:	https://hdl.handle.net/10356/103835 http://hdl.handle.net/10220/25855
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Institution:	Nanyang Technological University
Language:	English

id	sg-ntu-dr.10356-103835
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spelling	sg-ntu-dr.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.
institution	Nanyang Technological University
building	NTU Library
country	Singapore
collection	DR-NTU
language	English
topic	DRNTU::Science::Chemistry::Organic chemistry
spellingShingle	DRNTU::Science::Chemistry::Organic chemistry Bates, Roderick Wayland Lim, Chia Juan Collier, Steven J. Sukumaran, Joly Synthesis of (−)-deoxynupharidine by allenic hydroxylamine cyclisation
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.
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
format	Article
author	Bates, Roderick Wayland Lim, Chia Juan Collier, Steven J. Sukumaran, Joly
author_sort	Bates, Roderick Wayland
title	Synthesis of (−)-deoxynupharidine by allenic hydroxylamine cyclisation
title_short	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_sort	synthesis of (−)-deoxynupharidine by allenic hydroxylamine cyclisation
publishDate	2015
url	https://hdl.handle.net/10356/103835 http://hdl.handle.net/10220/25855
_version_	1681034884104060928

Synthesis of (−)-deoxynupharidine by allenic hydroxylamine cyclisation

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