Palladium-catalysed cyclisation of α-hydroxy allylic acetates: A formal synthesis of (±)-swainsonine

Roderick W. Bates; Mark R. Dewey; Chi H. Tang; Shahidah Bte Safii; Yanhan Hong; Jolyn Ke Hui Hsieh; Pei Shan Siah

doi:10.1055/s-0030-1260952

Palladium-catalysed cyclisation of α-hydroxy allylic acetates: A formal synthesis of (±)-swainsonine

Roderick W. Bates^*, Mark R. Dewey, Chi H. Tang, Shahidah Bte Safii, Yanhan Hong, Jolyn Ke Hui Hsieh, Pei Shan Siah

^*Corresponding author for this work

Nanyang Technological University

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

11 Citations (Scopus)

Abstract

A hydroxy group in the allylic position directed the stereochemistry of cyclisation of allylic acetates to form nitrogen heterocycles, giving the trans isomer for the piperidine and the cis isomer for the pyrrolidine. A formal synthesis of (±)-swainsonine was achieved.

Original language	English
Article number	D12711ST
Pages (from-to)	2053-2055
Number of pages	3
Journal	Synlett
Issue number	14
DOIs	https://doi.org/10.1055/s-0030-1260952
Publication status	Published - 2011
Externally published	Yes

ASJC Scopus Subject Areas

Organic Chemistry

Keywords

alkaloid
cyclisation
palladium
piperidine
pyrrolidine

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title = "Palladium-catalysed cyclisation of α-hydroxy allylic acetates: A formal synthesis of (±)-swainsonine",

abstract = "A hydroxy group in the allylic position directed the stereochemistry of cyclisation of allylic acetates to form nitrogen heterocycles, giving the trans isomer for the piperidine and the cis isomer for the pyrrolidine. A formal synthesis of (±)-swainsonine was achieved.",

keywords = "alkaloid, cyclisation, palladium, piperidine, pyrrolidine",

author = "Bates, {Roderick W.} and Dewey, {Mark R.} and Tang, {Chi H.} and Safii, {Shahidah Bte} and Yanhan Hong and Hsieh, {Jolyn Ke Hui} and Siah, {Pei Shan}",

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T2 - A formal synthesis of (±)-swainsonine

AU - Bates, Roderick W.

AU - Dewey, Mark R.

AU - Tang, Chi H.

AU - Safii, Shahidah Bte

AU - Hong, Yanhan

AU - Hsieh, Jolyn Ke Hui

AU - Siah, Pei Shan

PY - 2011

Y1 - 2011

N2 - A hydroxy group in the allylic position directed the stereochemistry of cyclisation of allylic acetates to form nitrogen heterocycles, giving the trans isomer for the piperidine and the cis isomer for the pyrrolidine. A formal synthesis of (±)-swainsonine was achieved.

AB - A hydroxy group in the allylic position directed the stereochemistry of cyclisation of allylic acetates to form nitrogen heterocycles, giving the trans isomer for the piperidine and the cis isomer for the pyrrolidine. A formal synthesis of (±)-swainsonine was achieved.

KW - alkaloid

KW - cyclisation

KW - palladium

KW - piperidine

KW - pyrrolidine

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ER -

Palladium-catalysed cyclisation of α-hydroxy allylic acetates: A formal synthesis of (±)-swainsonine

Abstract

ASJC Scopus Subject Areas

Keywords

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