Journal of the American Chemical Society, Vol.132, No.28, 9567-9569, 2010
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 C-8 hydroxymethylene functionality with retention of stereochemistry and the stereoselective installation of the C-13 methyl group through hydrogenation with homogeneous catalyst.