Ring closing metathesis/fragmentation route to (Z)-configured medium ring cycloalkenes. Total synthesis of (+/-)-periplanone C.
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.
Matovic
Radomir
R
Faculty of Chemistry, University of Belgrade, Studentski trg 16, 11000 Belgrade, Serbia.
Ivkovic
Aleksandar
A
Manojlovic
Marija
M
Tokic-Vujosevic
Zorana
Z
Saicic
Radomir N
RN
D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D003516:Cycloparaffins / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
D000475:Alkenes; D003516:Cycloparaffins; C496155:periplanone C