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Two-directional synthesis and biological evaluation of alkaloid 5-epi-cis-275B′

Procopiou, George; Aggarwal, Pooja; Newton, Annabella F.; Richards, David; Mellor, Ian R.; Harbottle, Gareth; Stockman, Robert A.

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Authors

George Procopiou

Pooja Aggarwal

Annabella F. Newton

David Richards

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IAN MELLOR IAN.MELLOR@NOTTINGHAM.AC.UK
Assistant Professor

Gareth Harbottle

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ROBERT STOCKMAN robert.stockman@nottingham.ac.uk
Professor of Organic Chemistry



Abstract

© 2014 The Royal Society of Chemistry. The first total synthesis of myrmicine ant alkaloid 5-epi-cis-275B′ (4) is presented. A tandem cyclisation established the entire core of the structure in a single transformation as well as the required 2,5-anti stereochemistry. Two-directional synthesis was used to furnish the cyclisation precursor 2, as in each of the subsequent steps towards the natural product. The first electrophysiology studies for 4 (against nicotinic acetylcholine receptors) were also conducted, finding modest inhibition of current.

Citation

Procopiou, G., Aggarwal, P., Newton, A. F., Richards, D., Mellor, I. R., Harbottle, G., & Stockman, R. A. (2014). Two-directional synthesis and biological evaluation of alkaloid 5-epi-cis-275B′. Chemical Communications, 50(97), 15355-15357. https://doi.org/10.1039/c4cc07287a

Journal Article Type Article
Acceptance Date Oct 15, 2014
Online Publication Date Oct 15, 2014
Publication Date Oct 15, 2014
Deposit Date Jan 26, 2017
Publicly Available Date Jan 26, 2017
Journal Chemical Communications
Print ISSN 1359-7345
Electronic ISSN 1364-548X
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 50
Issue 97
Pages 15355-15357
DOI https://doi.org/10.1039/c4cc07287a
Public URL https://nottingham-repository.worktribe.com/output/738196
Publisher URL http://pubs.rsc.org/en/Content/ArticleLanding/2014/CC/C4CC07287A#!divAbstract
Additional Information : This document is CrossCheck deposited; : Supplementary Information; : George Procopiou (ResearcherID); : Pooja Aggarwal (ORCID); : Pooja Aggarwal (ResearcherID); : The Royal Society of Chemistry has an exclusive publication licence for this journal; OPEN ACCESS: The accepted version of this article will be made freely available after a 12 month embargo period; : Received 15 September 2014; Accepted 15 October 2014; Accepted Manuscript published 15 October 2014; Advance Article published 28 October 2014; Version of Record published 11 November 2014
Contract Date Jan 26, 2017

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