title: A five-step synthesis of (S)-macrostomine from (S)-nicotine.
abstract: A concise synthesis of (S)-macrostomine has been accomplished in five steps from natural nicotine in 19% overall yield via a pyridyne Diels-Alder cycloaddition reaction as the key step. A Kumada cross-coupling reaction on a 1-chloroisoquinoline intermediate provided the natural product.
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA.
authors.forename: Monica F
authors.initials: MF
authors.lastname: Enamorado
authors.forename: Pauline W
authors.initials: PW
authors.lastname: Ondachi
authors.forename: Daniel L
authors.initials: DL
authors.lastname: Comins
mesh_terms: D007546:Isoquinolines / Q000138:chemical synthesis*; D015394:Molecular Structure; D009538:Nicotine / Q000737:chemistry*
chemical_list: D007546:Isoquinolines; C555150:macrostomine; D009538:Nicotine