title: A short total synthesis of (±)-epimeloscine and (±)-meloscine enabled by a cascade radical annulation of a divinylcyclopropane.
abstract: The first stereoselective synthesis of epimeloscine has been accomplished in 13 total steps with a longest linear sequence of 10 steps. The core of the synthesis takes only five steps, the key ones being acylation, stereoselective tandem radical cyclization of a divinylcyclopropane to make two rings, and group-selective ring-closing metathesis of the resulting divinylcyclopentane to make the last ring.
authors.affiliation: Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
authors.forename: Hanmo
authors.initials: H
authors.lastname: Zhang
authors.forename: Dennis P
authors.initials: DP
authors.lastname: Curran
mesh_terms: D000215:Acylation; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis*; D011804:Quinolines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D003521:Cyclopropanes; D011083:Polycyclic Compounds; D011804:Quinolines; D014753:Vinyl Compounds; C530682:meloscine; C030797:cyclopropane