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1,3-Diaxially Substituted trans-Decalins: Potential Nonsteroidal Human Progesterone Receptor Inhibitors

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posted on 03.10.2008, 00:00 by Ze Li, E. Blake Watkins, Hua Liu, Amar G. Chittiboyina, Paulo B. Carvalho, Mitchell A. Avery
On the basis of molecular modeling and QSAR analysis of the known human progesterone receptor (hPR) inhibitor Mifepristone (RU-486) and other hPR ligands, a new class of potential nonsteroidal hPR inhibitors was designed. The parent racemic compound 1 was synthesized through an efficient 13-step synthetic pathway. The key constructive steps are a stereoselective epoxide ring opening and the reductive Heck cyclization to form the main framework of (±)-1. The current established flexible synthetic route allows for further chemical diversification.