title: Ring closing metathesis/fragmentation route to (Z)-configured medium ring cycloalkenes. Total synthesis of (+/-)-periplanone C.
abstract: The combination of ring closing metathesis and beta-fragmentation offers an efficient entry into (Z)-configured medium ring cycloalkenes. The fragmentation step can be effected under anionic or radical conditions. The versatility of this method is demonstrated by the total synthesis of (+/-)-periplanone C-a macrocyclic pheromone of Periplaneta americana.
authors.affiliation: Faculty of Chemistry, University of Belgrade, Studentski trg 16, 11000 Belgrade, Serbia.
authors.forename: Radomir
authors.initials: R
authors.lastname: Matovic
authors.forename: Aleksandar
authors.initials: A
authors.lastname: Ivkovic
authors.forename: Marija
authors.initials: M
authors.lastname: Manojlovic
authors.forename: Zorana
authors.initials: Z
authors.lastname: Tokic-Vujosevic
authors.forename: Radomir N
authors.initials: RN
authors.lastname: Saicic
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D003516:Cycloparaffins / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D003516:Cycloparaffins; C496155:periplanone C