The University of Southampton
University of Southampton Institutional Repository

Synthetic studies towards the core structure of nakadomarin A by a thioamide-based strategy

Synthetic studies towards the core structure of nakadomarin A by a thioamide-based strategy
Synthetic studies towards the core structure of nakadomarin A by a thioamide-based strategy
The tricyclic BCD substructure of the marine natural product nakadomarin A has been synthesised. The strategy utilised a key carbon-carbon bond-forming reaction between a furan and an N-acyliminium ion derived from a secondary thiolactam. In addition, a novel three-component coupling reaction between a thioamide, an allylic bromide and an isocyanate, leading to the establishment of two new stereogenic centres, is reported.

natural products, alkaloids, sigmatropic rearrangement, multicomponent reactions
1434-193X
129-139
Chavda, Jai K.
e82174c3-7a66-4cc3-91ed-a26d4c44fa15
Procopiou, Panayiotis A.
1f9db1f1-e6bc-426f-8bd9-32051ce79a7d
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Porter, Michael J.
bcb65cd0-08f3-40bd-b876-77dc2a004091
Chavda, Jai K.
e82174c3-7a66-4cc3-91ed-a26d4c44fa15
Procopiou, Panayiotis A.
1f9db1f1-e6bc-426f-8bd9-32051ce79a7d
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Porter, Michael J.
bcb65cd0-08f3-40bd-b876-77dc2a004091

Chavda, Jai K., Procopiou, Panayiotis A., Horton, Peter N., Coles, Simon J. and Porter, Michael J. (2014) Synthetic studies towards the core structure of nakadomarin A by a thioamide-based strategy. European Journal of Organic Chemistry, 2014 (1), 129-139. (doi:10.1002/ejoc.201301063).

Record type: Article

Abstract

The tricyclic BCD substructure of the marine natural product nakadomarin A has been synthesised. The strategy utilised a key carbon-carbon bond-forming reaction between a furan and an N-acyliminium ion derived from a secondary thiolactam. In addition, a novel three-component coupling reaction between a thioamide, an allylic bromide and an isocyanate, leading to the establishment of two new stereogenic centres, is reported.

Text
pdf - Version of Record
Available under License Other.
Download (13kB)

More information

e-pub ahead of print date: 14 November 2013
Published date: January 2014
Keywords: natural products, alkaloids, sigmatropic rearrangement, multicomponent reactions
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry

Identifiers

Local EPrints ID: 362483
URI: http://eprints.soton.ac.uk/id/eprint/362483
ISSN: 1434-193X
PURE UUID: ce02c6c0-5e4e-42f2-a9ee-dfc2458a24c5
ORCID for Peter N. Horton: ORCID iD orcid.org/0000-0001-8886-2016
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 25 Feb 2014 13:54
Last modified: 18 Feb 2021 16:54

Export record

Altmetrics

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.

×