We planned to construct the 10-oxa-tricyclo[5.3.1.03,8]undecan-9-one structure fused with indolenine, the core skeleton of 1, by linking C7 and C16 via intramolecular oxidative coupling in the late stage. Although several examples of intramolecular oxidative coupling between activated a-carbonyl carbon and indole C3 have been reported, there is no case involving a non-activated lactone. In order to obtain the information for the synthesis of scholarisine A (1), we examined to synthesize 4which is a model compund of 1.