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.
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Zhang et al. (2010) studied this question.
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