title: β-Hydroxy-γ-lactones as nucleophiles in the Nicholas reaction for the synthesis of oxepene rings. Enantioselective formal synthesis of (-)-isolaurepinnacin and (+)-rogioloxepane A.
abstract: The enantioselective formal synthesis of (-)-isolaurepinnacin and (+)-rogioloxepane A has been achieved. The key steps are an intermolecular Nicholas reaction with a β-hydroxy-γ-lactone as the nucleophile, to form branched linear ethers, and an olefin ring-closing metathesis to obtain the oxepene core.
authors.affiliation: Instituto Universitario de Bio-Orgánica "Antonio González", CIBICAN, Departamento de Química Orgánica, Universidad de La Laguna (ULL), Avda. Francisco Sánchez 2, 38206 La Laguna, Tenerife, Spain. vmartin@ull.es.
authors.forename: Julio
authors.initials: J
authors.lastname: Rodríguez-López
authors.forename: Nuria
authors.initials: N
authors.lastname: Ortega
authors.forename: Victor S
authors.initials: VS
authors.lastname: Martín
authors.forename: Tomás
authors.initials: T
authors.lastname: Martín
mesh_terms: D007783:Lactones / Q000737:chemistry*; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D010082:Oxepins; C000592870:isolaurepinnacin; C478288:rogioloxepane A