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J Org Chem


Title:Ring closing metathesis/fragmentation route to (Z)-configured medium ring cycloalkenes. Total synthesis of (+/-)-periplanone C
Author(s):Matovic R; Ivkovic A; Manojlovic M; Tokic-Vujosevic Z; Saicic RN;
Address:"Faculty of Chemistry, University of Belgrade, Studentski trg 16, 11000 Belgrade, Serbia"
Journal Title:J Org Chem
Year:2006
Volume:71
Issue:25
Page Number:9411 - 9419
DOI: 10.1021/jo061790j
ISSN/ISBN:0022-3263 (Print) 0022-3263 (Linking)
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
Keywords:"Alkenes/*chemistry Cyclization Cycloparaffins/*chemical synthesis Magnetic Resonance Spectroscopy Spectrometry, Mass, Electrospray Ionization Stereoisomerism;"
Notes:"MedlineMatovic, Radomir Ivkovic, Aleksandar Manojlovic, Marija Tokic-Vujosevic, Zorana Saicic, Radomir N eng Research Support, Non-U.S. Gov't 2006/12/02 J Org Chem. 2006 Dec 8; 71(25):9411-9. doi: 10.1021/jo061790j"

 
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