title: Synthesis of the cyclohexane core of phomactins and a new route to the bicyclo[9.3.1]pentadecane diterpenoid skeleton.
abstract: Conjugate reduction of an enone accompanied by in situ intramolecular aldol condensation was used to construct the tetrasubstituted cyclohexane nucleus of phomactins. Subsequent relay ring-closing metathesis completed the nine-membered ansa bridge of the diterpenoid framework.
authors.affiliation: Department of Chemistry, Oregon State University, Corvallis, Oregon 97331, USA.
authors.forename: Keith D
authors.initials: KD
authors.lastname: Schwartz
authors.forename: James D
authors.initials: JD
authors.lastname: White
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D001643:Bridged Bicyclo Compounds; D003510:Cyclohexanes; D004224:Diterpenes; C033245:pentadecane; C506365:Cyclohexane