Ring-closing metathesis/fragmentation route to geometrically defined medium-ring cycloalkenes: total synthesis of (+/-)-periplanone C.
The combination of alkene metathesis and beta-fragmentation offers an efficient entry into (Z)-configured medium-ring cycloalkenes. The versatility of this method is demonstrated by the total synthesis of Periplanone C, a semiochemical of Periplaneta americana. [reaction: see text]
Ivkovic
Aleksandar
A
Faculty of Chemistry, University of Belgrade, Studentski trg 16, P.O. Box 158, 11000 Belgrade, Serbia and Montenegro.
Matovic
Radomir
R
Saicic
Radomir N
RN
D000818:Animals; D003432:Cross-Linking Reagents / Q000737:chemistry*; D003500:Cyclization; D003516:Cycloparaffins / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010526:Periplaneta / Q000737:chemistry*; D013237:Stereoisomerism
D003432:Cross-Linking Reagents; D003516:Cycloparaffins; C496155:periplanone C