A synthesis of tetracyclo[5,3,1,1^2,6,0^4,9]dodecane (iceane)

Abstract

A description is given of the chemistry which led to the synthesis of the title compound (1). Key intermediate compounds in this synthetic route were tricyclo[5,3,1,0^4,9]undec-5-en-2-one (13), tricyclo[5,3,1,0^4,9]undec-2-en-endo-6-ylmethanol (36) and the exo and endo isomers of chloroiceane (42) and (44). Compound (42) must have a chlorine atom in the prow position of one of the three rings in boat configurations.