title: Enantiospecific approach toward pentalenolactone.
abstract: [reaction: see text] The enantiospecific assembly of the pentalenolactones' carbon skeleton was achieved in 17 steps and 16% overall yield from methyl alpha-D-glucopyranoside. The synthetic strategy relies on two highly efficient key steps: an exo-diastereoselective Diels-Alder reaction and a nonsymmetric ozonolysis.
authors.affiliation: Instituto de Química Organica de Síntesis, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, CONICET, Suipacha 531, S2002LRK Rosario, Argentina.
authors.forename: Sebastian A
authors.initials: SA
authors.lastname: Testero
authors.forename: Rolando A
authors.initials: RA
authors.lastname: Spanevello
mesh_terms: D005960:Glucosides / Q000737:chemistry*; D015394:Molecular Structure; D010126:Ozone / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005960:Glucosides; D012717:Sesquiterpenes; C017996:arenaemycin E; D010126:Ozone