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

摘要

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.