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.