A short route to 'reverse-prenylated' pyrrolo[2,3-b]indoles via tandem olefination and Claisen rearrangement of 2-(3,3-dimethylallyloxy)indol-3-ones: First total synthesis of flustramine C

Article abstract of DOI:10.1016/0040-4039(96)01690-5

The Wittig or Horner-Emmons reaction of 1-acetyl-2-(3,3-dimethylallyloxy)indol-3-ones proceeded via tandem olefination, isomerization, Claisen rearrangement, and deacetylation to give 3-cyanomethyl-3-(1,1-dimethylallyl)indol-2-ones in good yields, which were reduced with Red-Al to afford pyrrolo[2,3-b]indoles having the 1,1-dimethylallyl group at the 3a-position. The first total synthesis of the marine alkaloid flustramine C was also described.