Synthesis of the indole alkaloid isolated from the marine sponge Halichondria melanodocia.

We describe the first successful synthesis of the indole alkaloid isolated from the marine sponge Halichondria melanodocia , using the previously unreported nickel catalyzed cross electrophile coupling of an α-bromoketone to a sp 2 iodide to provide a convergent synthesis of the carbon framework without concomitant olefin migration. The indole alkaloid was thus synthesized in two steps from known compounds. [Display omitted] • Our paper reports the first synthesis of the indole alkaloid from the marine sponge Halichondria melanodocia. [ABSTRACT FROM AUTHOR]