A novel cascade cyclisation protocol has been developed which â zips upâ two rings to form new tetracycles. In the protocol, treatment of vinyl bromides and iodides with hexamethylditin (Me3Sn.rad;) yields intermediate vinyl radicals which undergo 5-exo cyclisation onto nitrile groups to yield intermediate iminyl radicals. The iminyl radicals can undergo 6-endo cyclisation (or 5-exo followed by neophyl rearrangement) to yield tetracyclic Ï -radicals which lose hydrogen (H.rad;) in an H-abstraction step. Methyl radicals, generated from the breakdown of trimethylstannyl radicals (Me3Sn.rad;), are proposed as a possible H-abstractor for this final oxidative step. The protocol has been used to synthesise the tetracyclic rings Aâ D (tetracycle indolizino[1,2-b]quinolin-9(11H)-one) of the anticancer alkaloids camptothecin, mappicine, nothapodytine B and nothapodytine A. The protocol has also been applied to the synthesis of analogues of camptothecin in which ring A has been replaced by thiophene (8,10-dihydrothieno[2â ²,3â ²:5,6]pyrido[2,3-a]indolizin-8-one) and ring D by pyrrole (10H-pyrrolizino[1,2-b]quinoline) and benzene (11H-indeno[1,2-b]quinolin-11-one).