title: Preparation of oxocene terpenes. The first enantiospecific synthesis of cytotoxic arenaran A.
abstract: The first syntheses of cytotoxic marine arenarans A and B starting from commercial (-)-sclareol are reported. The oxocene ring of the target compound is formed via ring-closing metathesis, a process that depends on certain structural requirements. The trans-fused structure of the natural product is confirmed by comparison with the cis-fused isomer, which was synthesized. This synthetic strategy is also applicable to the synthesis of other oxocene terpenes.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain. rachid@ugr.es eamr@ugr.es.
authors.forename: Alejandro
authors.initials: A
authors.lastname: Torres
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain. rachid@ugr.es eamr@ugr.es.
authors.forename: Pilar
authors.initials: P
authors.lastname: Gutierrez
authors.affiliation: Area de Química Orgánica, Departamento de Química y Física, Universidad de Almería, 04120 Almería, Spain.
authors.forename: Ramón
authors.initials: R
authors.lastname: Alvarez-Manzaneda
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain. rachid@ugr.es eamr@ugr.es.
authors.forename: Rachid
authors.initials: R
authors.lastname: Chahboun
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain. rachid@ugr.es eamr@ugr.es.
authors.forename: Enrique
authors.initials: E
authors.lastname: Alvarez-Manzaneda
mesh_terms: D060326:Chemistry Techniques, Synthetic; D003500:Cyclization; D003603:Cytotoxins / Q000138:chemical synthesis* / Q000737:chemistry*; D035964:Oxocins / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003603:Cytotoxins; D035964:Oxocins; D012717:Sesquiterpenes; C093755:arenaran A