Synthetic Studies on Cimiciduphytine

Synthetic studies on a dimeric indole alkaloid, cimiciduphytine, were conducted based on modifying our synthesis of (+)-haplophytine. The key feature of this synthesis is the development of chemoselective deallylation of an N,O-diallyl derivative of a hydroxy aniline derivative, and copper sulfate-mediated oxidative lactonization via oxidation of the amino moiety. A highly convergent strategy led us to synthesize the originally proposed cimiciduphytine. However, the compound was unstable under air and underwent cyclization to generate a bridged derivative.