Enantioselective Synthesis of a Highly Substituted Tetrahydrofluorene Derivative as a Potent and Selective Estrogen Receptor Beta Agonist

…, E Cleator, A Dieguez-Vazquez, A Gibb…

Index: Maddess, Matthew L.; Scott, Jeremy P.; Alorati, Anthony; Baxter, Carl; Bremeyer, Nadine; Brewer, Sarah; Campos, Kevin; Cleator, Ed; Dieguez-Vazquez, Alejandro; Gibb, Andrew; Gibson, Andrew; Howard, Melissa; Keen, Stephen; Klapars, Artis; Lee, Jaemoon; Li, Jing; Lynch, Joseph; Mullens, Peter; Wallace, Debra; Wilson, Robert Organic Process Research and Development, 2014 , vol. 18, # 4 p. 528 - 538

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Citation Number: 7

Abstract

The development and execution of a practical asymmetric synthesis of the estrogen receptor beta selective agonist (8 R, 10a S)-6-(trifluoromethyl)-8, 9, 10, 11-tetrahydro-8, 10a- methanocyclohepta [1, 2] indeno [4, 5-d][1, 2, 3] triazol-7 (3 H)-one is described. The optimized route features a key chiral auxiliary-mediated dialkylation approach to set the all- carbon quaternary center with exceptional stereocontrol. Overall, the chemistry has been ...