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Synthetic Studies Towards the Core Structure of Nakadomarin A by a Thioamide-Based Strategy

Chavda, JK; Procopiou, PA; Horton, PN; Coles, SJ; Porter, MJ; (2014) Synthetic Studies Towards the Core Structure of Nakadomarin A by a Thioamide-Based Strategy. European Journal Of Organic Chemistry , 2014 (1) 129 - 139. 10.1002/ejoc.201301063. Green open access

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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.

Type: Article
Title: Synthetic Studies Towards the Core Structure of Nakadomarin A by a Thioamide-Based Strategy
Open access status: An open access version is available from UCL Discovery
DOI: 10.1002/ejoc.201301063
Publisher version: http://dx.doi.org/10.1002/ejoc.201301063
Language: English
Additional information: © 2014 The Authors. Published by WILEY-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Keywords: Natural products, Alkaloids, Sigmatropic rearrangement, Multicomponent reactions
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/1421004
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