The pyrroloiminoquinone alkaloid family consisting of discorhabdins and makaluvamines exhibits antitumor activities derived from their unique highly-fused structures. The total synthesis of them and the key reactions used in the total synthesis of these compounds are described. 3 (86%) 1 : R=H 2 : R=TMS Het 4 low yield Pyrroloiminoquinone Alkaloids Current Organic Chemistry, 2005, Vol. 9, No. 15 1569