Synthesis of (-)-Deoxynupharidine by Allenic Hydroxylamine Cyclisation

Roderick W. Bates; Chia Juan Lim; Steven J. Collier; Joly Sukumaran

doi:10.1002/ajoc.201500094

Synthesis of (-)-Deoxynupharidine by Allenic Hydroxylamine Cyclisation

Roderick W. Bates^*, Chia Juan Lim, Steven J. Collier, Joly Sukumaran

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	652-658
Number of pages	7
Journal	Asian Journal of Organic Chemistry
Volume	4
Issue number	7
DOIs	https://doi.org/10.1002/ajoc.201500094
Publication status	Published - Jul 1 2015
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

ASJC Scopus Subject Areas

Organic Chemistry

Keywords

(-)-deoxynupharidine
Allenes
Hydroxylamines
Nuphar alkaloids
Total synthesis

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10.1002/ajoc.201500094

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title = "Synthesis of (-)-Deoxynupharidine by Allenic Hydroxylamine Cyclisation",

abstract = "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.",

keywords = "(-)-deoxynupharidine, Allenes, Hydroxylamines, Nuphar alkaloids, Total synthesis",

author = "Bates, {Roderick W.} and Lim, {Chia Juan} and Collier, {Steven J.} and Joly Sukumaran",

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doi = "10.1002/ajoc.201500094",

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AU - Bates, Roderick W.

AU - Lim, Chia Juan

AU - Collier, Steven J.

AU - Sukumaran, Joly

PY - 2015/7/1

Y1 - 2015/7/1

N2 - 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.

AB - 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.

KW - (-)-deoxynupharidine

KW - Allenes

KW - Hydroxylamines

KW - Nuphar alkaloids

KW - Total synthesis

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JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 7

ER -

Synthesis of (-)-Deoxynupharidine by Allenic Hydroxylamine Cyclisation

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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