Total Synthesis of (±)-Aplykurodinone-1: Traceless Stereochemical Guidance

The total synthesis of the highly degraded steroidal natural product, aplykurodinone-1 (1), has been accomplished. Key features include a one-flask hydrolysis/retro-aldol/iodolactonization sequence to excise the C₈ hydroxymethylene functionality with retention of stereochemistry and the stereoselective installation of the C₁₃ methyl group through hydrogenation with homogeneous catalyst.