title: Synthesis of the norjatrophane diterpene (-)-15-acetyl-3-propionyl- 17-norcharaciol.
abstract: [reaction: see text] A scalable enantioselective synthesis of the nonnatural 17-norjatrophane diterpene 3-propionyl-15-acetyl-17-norcharaciol is described. Key C/C-connecting transformations are an Evans aldol reaction, an intramolecular carbonyl ene reaction, a Horner-Wadsworth-Emmons olefination, and a ring-closing metathesis for the formation of a 12-membered carbacycle.
authors.affiliation: Fachrichtung Chemie, Technische Universität Dresden, D-01062 Dresden, Germany.
authors.forename: Hannes
authors.initials: H
authors.lastname: Helmboldt
authors.forename: Daniel
authors.initials: D
authors.lastname: Köhler
authors.forename: Martin
authors.initials: M
authors.lastname: Hiersemann
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C516000:15-acetyl-3-propionyl-17-norcharaciol; D000475:Alkenes; D004224:Diterpenes