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

The first total synthesis of myrmicine ant alkaloid 5-epi-cis-275B0 (4) is presented. A tandem cyclisation stablished 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...

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Bibliographic Details
Main Authors: Procopiou, George, Aggarwal, Pooja, Newton, Annabella F., Richards, David, Mellor, Ian R., Harbottle, Gareth, Stockman, Robert A.
Format: Article
Published: Royal Society of Chemistry 2014
Online Access:https://eprints.nottingham.ac.uk/34270/
Description
Summary:The first total synthesis of myrmicine ant alkaloid 5-epi-cis-275B0 (4) is presented. A tandem cyclisation stablished 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.