title: Divergent pathways to furosesquiterpenes: first total syntheses of (+)-zedoarol and (Rac)-gweicurculactone.
abstract: A non-natural hydroxy-elemane was found amenable to divergent transformations, producing either polyunsaturated guaianes under basic, oxygen-free conditions, or oxidized furogermacranes when anionic oxy-Cope reaction quenched by an oxidant is employed. Based on these findings, the first total syntheses of zedoarol and gweicurculactone are reported.
authors.affiliation: Aristotle University of Thessaloniki, Department of Chemistry, Laboratory of Organic Chemistry, University Campus, 54124 Thessaloniki, Greece. alzograf@chem.auth.gr.
authors.forename: Elissavet E
authors.initials: EE
authors.lastname: Anagnostaki
authors.forename: Vera P
authors.initials: VP
authors.lastname: Demertzidou
authors.forename: Alexandros L
authors.initials: AL
authors.lastname: Zografos
mesh_terms: D052176:Azulenes / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D045789:Sesquiterpenes, Guaiane / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D052176:Azulenes; D005663:Furans; D007783:Lactones; D012717:Sesquiterpenes; D045789:Sesquiterpenes, Guaiane; C421026:guaiane; C000601582:zedoarol; C062413:gweicurculactone; C039281:furan