The University of Southampton
University of Southampton Institutional Repository

Total synthesis of the Tetracyclic Lupin Alkaloid (+)-Allomatrine

Total synthesis of the Tetracyclic Lupin Alkaloid (+)-Allomatrine
Total synthesis of the Tetracyclic Lupin Alkaloid (+)-Allomatrine
(+)-Allomatrine has been synthesised using an imino-aldol reaction and N-acyliminium cyclisation as key steps. Strategically, use of the tert-butylsulfinimine derivative of (E)-4-(trimethylsilyl)but-2-enal enables the staged formation of 3 C—C bonds, a C—N bond and the four stereogenic centres within the target.
1523-7060
4596-4599
Watkin, Samuel V.
e30119fd-05e0-4a0e-9c35-e393e8a59ab2
Camp, Nicholas P.
4f21b310-272b-4c01-8c6b-60d36046cb28
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Watkin, Samuel V.
e30119fd-05e0-4a0e-9c35-e393e8a59ab2
Camp, Nicholas P.
4f21b310-272b-4c01-8c6b-60d36046cb28
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5

Watkin, Samuel V., Camp, Nicholas P. and Brown, Richard C.D. (2013) Total synthesis of the Tetracyclic Lupin Alkaloid (+)-Allomatrine. Organic Letters, 15 (17), 4596-4599. (doi:10.1021/ol402198n).

Record type: Article

Abstract

(+)-Allomatrine has been synthesised using an imino-aldol reaction and N-acyliminium cyclisation as key steps. Strategically, use of the tert-butylsulfinimine derivative of (E)-4-(trimethylsilyl)but-2-enal enables the staged formation of 3 C—C bonds, a C—N bond and the four stereogenic centres within the target.

This record has no associated files available for download.

More information

Published date: 27 August 2013
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 356452
URI: http://eprints.soton.ac.uk/id/eprint/356452
ISSN: 1523-7060
PURE UUID: 623e90ac-895c-4e67-825b-4d19922d7264
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

Catalogue record

Date deposited: 30 Sep 2013 14:47
Last modified: 15 Mar 2024 02:53

Export record

Altmetrics

Contributors

Author: Samuel V. Watkin
Author: Nicholas P. Camp

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×