title: Stereoselective Synthesis of 2,15-Dihydroxycalamenene and 2-Methoxycalamenene. Determination of the Configuration of Natural 2,15-Dihydroxycalamenene.
abstract: The enantioselective preparation of the two diastereoisomeric forms of 2,15-dihydroxycalamelene and 2-methoxycalamenene is here described. The (7S,10R) and (7R,10R) isomers of these natural products were synthesized starting from (5R,8S)-methyl-4-hydroxy-8-isopropyl-5-methyl-5,6,7,8-tetrahydronaphthalene-2-carboxylate and (5R,8R)-methyl-4-hydroxy-8-isopropyl-5-methyl-5,6,7,8-tetrahydronaphthalene-2-carboxylate, respectively, in turn preparable from (-)-menthone and (+)-isomenthone. The NMR analysis of the obtained sesquiterpenes allow assigning (7R,10S) absolute configuration to the natural occurring 2,15-dihydroxycalamelene.
authors.forename: Stefano
authors.initials: S
authors.lastname: Serra
mesh_terms: D015394:Molecular Structure; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D013729:Terpenes; C502644:calamenene; C473635:hydroxycalamenene