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
129-139
Chavda, Jai K.
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Procopiou, Panayiotis A.
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Horton, Peter N.
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Coles, Simon J.
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Porter, Michael J.
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January 2014
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), .
(doi:10.1002/ejoc.201301063).
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.
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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
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Date deposited: 25 Feb 2014 13:54
Last modified: 15 Mar 2024 03:04
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Contributors
Author:
Jai K. Chavda
Author:
Panayiotis A. Procopiou
Author:
Peter N. Horton
Author:
Michael J. Porter
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