title: Synthesis of guaia-4(5)-en-11-ol, guaia-5(6)-en-11-ol, aciphyllene, 1-epi-melicodenones C and E, and other guaiane-type sesquiterpenoids via the diastereoselective epoxidation of guaiol.
abstract: The diastereomeric ratio of epoxidation of the internally bridged carbon-carbon double bond of guaiol (1a) is strongly influenced by the combined effects of the types of remote protecting groups on the hydroxyisopropyl side chain, choice of solvent, and epoxidizing reagent. This observation has allowed us to devise concise stereoselective syntheses of a range of guaiane-type sesquiterpenoids via an epoxidation, ring-opening/elimination, and functionality manipulation sequence. Natural products guaia-4(5)-en-11-ol (2a), guaia-5(6)-en-11-ol (3), and aciphyllene (4a) and epimers of the recently isolated natural products, 1-epi-guaia-4(5)-en-11-ol (2b), 1-epi-aciphyllene (4b), and 1-epi-melicodenones C (5a) and E (6a), were synthesized in good yields in relatively few steps.
authors.affiliation: School of Agriculture, Food and Wine, The University of Adelaide , Waite Campus, Glen Osmond 5064, Adelaide, South Australia, Australia.
authors.forename: An-Cheng
authors.initials: AC
authors.lastname: Huang
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Sumby
authors.forename: Edward R T
authors.initials: ER
authors.lastname: Tiekink
authors.forename: Dennis K
authors.initials: DK
authors.lastname: Taylor
mesh_terms: D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D045789:Sesquiterpenes, Guaiane / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D012717:Sesquiterpenes; D045789:Sesquiterpenes, Guaiane; C421026:guaiane; C469146:guaiol