N-methylwelwitindolinone C isothiocyanate is a complex alkaloid that was first isolated from the cyanobacterium Hapalosiphon welwitschii in 1994. The unique structure and promising biological activity of this natural product has prompted our laboratory to pursue its total synthesis.  In this presentation, the completed total synthesis of N-methylwelwitindolinone C isothiocyanate will be described. Our approach relies on the use of an indolyne cyclization to form the [4.3.1]-bicyclic framework of the natural product. The approach also utilizes a late-stage nitrene insertion to install the bridgehead nitrogen.

Total synthesis of (–)-N-methylwelwitindolinone  C isothiocyanate

243rd National Meeting (2012)

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