title: An unusual Michael-induced skeletal rearrangement of a bicyclo[3.3.1]nonane framework of phloroglucinols to a novel bioactive bicyclo[3.3.0]octane.
abstract: A novel skeletal rearrangement of bicyclo[3.3.1]nonane-2,4,9-trione (16) to an unprecedented highly functionalized bicyclo[3.3.0]octane system (17), induced by an intramolecular Michael addition, is presented. This novel framework was found to be similarly active to hyperforin (1), against PC-3 cell lines. A mechanistic study was examined in detail, proposing a number of cascade transformations. Also, reactivity of the Δ(7,10)-double bond was examined under several conditions to explain the above results.
authors.affiliation: Synthesis and Bioorganic Chemistry, NCSR "Demokritos" , 153 10 Ag. Paraskevi, Athens, Greece, Chemical Laboratories, Agricultural University of Athens , Iera Odos 75, 118 55, Athens, Greece, Crystal Engineering, Growth & Design Laboratory, Department of Chemistry, University of Crete , P.O. Box 2208, GR-71003 Heraklion, Crete, Greece, EPOS-Iasis, R&D , 5 Karyatidon Street, 2028, Nicosia, Cyprus, and University of Cyprus , 75 Kallipoleos Avenue, 1678 Nicosia, Cyprus.
authors.forename: Veroniki P
authors.initials: VP
authors.lastname: Vidali
authors.forename: Kornilia P
authors.initials: KP
authors.lastname: Mitsopoulou
authors.forename: Marianna
authors.initials: M
authors.lastname: Dakanali
authors.forename: Konstantinos D
authors.initials: KD
authors.lastname: Demadis
authors.forename: Andreani D
authors.initials: AD
authors.lastname: Odysseos
authors.forename: Yiota A
authors.initials: YA
authors.lastname: Christou
authors.forename: Elias A
authors.initials: EA
authors.lastname: Couladouros
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009795:Octanes / Q000737:chemistry*; D010696:Phloroglucinol / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D001643:Bridged Bicyclo Compounds; D009795:Octanes; D010696:Phloroglucinol; C017573:nonane; C026728:octane