Total Synthesis of (±)-Aplykurodinone-1: Traceless Stereochemical Guidance
- 1 June 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 132 (28), 9567-9569
- https://doi.org/10.1021/ja1035495
Abstract
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.Keywords
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