N-?Methylwelwitindolinone D isonitrile is a complex alkaloid that was first isolated from the cyanobacterium Fischerella major in 1999.  In this presentation, the completed total synthesis of N-?methylwelwitindolinone D isonitrile 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 and a nitrene insertion to install the bridgehead nitrogen. The approach also utilizes a late-stage introduction of the tetrahydrofuran moiety via a double C-H functionalization event.

Enantiospecific total synthesis of <i>N</i>-methylwelwitindolinone D isonitrile

248th National Meeting (2014)

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Enantiospecific total synthesis of N-methylwelwitindolinone D isonitrile