title: Non-natural elemane as the "stepping stone" for the synthesis of germacrane and guaiane sesquiterpenes.
abstract: The synthesis of hydroxyelemane 5 from (R)-carvone and its utilization as a common synthetic scaffold to produce structurally diverse germacrane and guaiane sesquiterpenes are described. A highly enantio- and stereoselective biomimetic tandem oxy-Cope/ene rearrangement was used as the key reaction to access the 10-membered macrocyclic core of germacranes and the condensed 5-7 carbocycles of guaiane sesquiterpenes. Additionally, reactions of furanoguaianes under acidic or oxidizing reagents have been investigated, and preliminary results of these conversions are presented.
authors.affiliation: Department of Chemistry, Laboratory of Organic Chemistry, Aristotle University of Thessaloniki, University Campus, 54124 Thessaloniki, Greece.
authors.forename: Elissavet E
authors.initials: EE
authors.lastname: Anagnostaki
authors.forename: Alexandros L
authors.initials: AL
authors.lastname: Zografos
mesh_terms: D003500:Cyclization; D000081005:Cyclohexane Monoterpenes; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry; D045789:Sesquiterpenes, Guaiane / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; D045789:Sesquiterpenes, Guaiane; C006923:carvone