Concise and highly convergent syntheses of antifungal marine bis(indole) alkaloids, hamacanthin A (I) and trans-2,5-bis(3'-indolyl)piperazine (II) is described. The total synthesis of hamacanthin A is accomplished via the oxidative amidation-chemoselective heterocycloannulation of 2,2-dibromo-1-(1H-indol-3-yl)ethanone with 1-(1H-indol-3-yl)ethane-1,2-diamine. The reduction of desbromo hamacanthin with aluminum borohydride afforded the alkaloid trans-2,5-bis(3'-indolyl)piperazine. Two novel and convenient protocols for the synthesis of indolyl-1,2-diaminoethane are also developed in moderate to good yields.