title: Two-directional synthesis and biological evaluation of alkaloid 5-epi-cis-275B'.
abstract: 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.
authors.affiliation: School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK. robert.stockman@nottingham.ac.uk.
authors.forename: George
authors.initials: G
authors.lastname: Procopiou
authors.forename: Pooja
authors.initials: P
authors.lastname: Aggarwal
authors.forename: Annabella F
authors.initials: AF
authors.lastname: Newton
authors.forename: David
authors.initials: D
authors.lastname: Richards
authors.forename: Ian R
authors.initials: IR
authors.lastname: Mellor
authors.forename: Gareth
authors.initials: G
authors.lastname: Harbottle
authors.forename: Robert A
authors.initials: RA
authors.lastname: Stockman
mesh_terms: D000109:Acetylcholine / Q000494:pharmacology; D000470:Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology*; D001688:Biological Products; D002460:Cell Line; D018679:Cholinergic Agonists / Q000494:pharmacology; D003500:Cyclization; D006801:Humans; D011804:Quinolines / Q000138:chemical synthesis* / Q000494:pharmacology*; D011978:Receptors, Nicotinic / Q000502:physiology*
chemical_list: D000470:Alkaloids; D001688:Biological Products; D018679:Cholinergic Agonists; D011804:Quinolines; D011978:Receptors, Nicotinic; D000109:Acetylcholine