title: Concise total synthesis of albaflavenone utilizing sequential intramolecular aldol condensation: determination of absolute configuration.
abstract: The first total synthesis of albaflavenone, a novel antibiotic sesquiterpene, has been accomplished via the concise construction of its zizaene skeleton utilizing sequential intramolecular aldol condensation followed by chemo- and diastereoselective reduction of the conjugated carbon-carbon double bond. This synthetic work was completed in nine steps from 2-cyclopenten-1-one as a starting material without the use of protecting groups and with high stereocontrol. In addition, the absolute configuration of naturally occurring albaflavenone was determined to be 1R,2S and 8S.
authors.affiliation: School of Life Sciences, Tokyo University of Pharmacy and Life Sciences , 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
authors.forename: Toyoharu
authors.initials: T
authors.lastname: Kobayashi
authors.forename: Yutaro
authors.initials: Y
authors.lastname: Kon
authors.forename: Hideki
authors.initials: H
authors.lastname: Abe
authors.forename: Hisanaka
authors.initials: H
authors.lastname: Ito
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D003517:Cyclopentanes; D012717:Sesquiterpenes; C087466:albaflavenone; C013905:cyclopentenone