American Chemical Society
ja1035495_si_003.txt (14.52 kB)

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

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posted on 2010-07-21, 00:00 authored by Yandong Zhang, Samuel J. Danishefsky
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.