1227479-83-5Relevant articles and documents
Development of a kilogram-scale asymmetric synthesis of a potent DP receptor antagonist
Tudge, Matthew,Savarin, Cecile G.,Difelice, Katherine,Maligres, Peter,Humphrey, Guy,Reamer, Bob,Tellers, David M.,Hughes, Dave
, p. 787 - 798 (2010)
An efficient asymmetric synthesis of a unique sulfenylated prostaglandin DP receptor antagonist candidate is described. The synthesis is characterized by a novel intramolecular Friedel-Crafts cyclization of an imino-pyrrole to prepare the azaindole core. Other key steps include a highly selective Horner-Wadsworth-Emmons olefination of a tricyclic ketone intermediate and subsequent catalytic asymmetric hydrogenation of a trisubstituted α,β-unsaturated ester to install the chirogenic center. Finally, a new indole sulfenylation protocol was developed to install the aromatic thioether functionality in good yield.
