1579951-58-8Relevant articles and documents
Enantioselective synthesis of a highly substituted tetrahydrofluorene derivative as a potent and selective estrogen receptor beta agonist
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
, p. 528 - 538 (2014/05/06)
The development and execution of a practical asymmetric synthesis of the estrogen receptor beta selective agonist (8R,10aS)-6-(trifluoromethyl)-8,9,10, 11-tetrahydro-8,10a-methanocyclohepta[1,2]indeno[4,5-d][1,2,3]triazol-7(3H)-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 used to prepare >30 kg of drug candidate in 21% overall yield through 13 longest linear steps and with >99% ee.
