136891-53-7Relevant academic research and scientific papers
Asymmetric Total Syntheses of Aetheramides and Their Stereoisomers: Stereochemical Assignment of Aetheramides
Qi, Na,Allu, Srinivasa Rao,Wang, Zhanlong,Liu, Qiang,Guo, Jian,He, Yun
, p. 4718 - 4721 (2016)
The concise total syntheses of the potent HIV inhibitors aetheramides A and B (IC50 values of 15 and 18 nM), as well as three pairs of their stereoisomers, were achieved, which allowed the complete stereochemical assignment of aetheramides for the first time. With a longest linear sequence of 15 steps, the convergent, fully stereocontrolled route provided aetheramides A and B in 5.3% and 3.6% yields, respectively. The synthetic strategy features efficient Stille coupling for macrocyclization, asymmetric aldol reactions to establish the ambiguous stereochemistries at C-17 and C-26, and implementation of mild conditions to avoid the epimerization of the sensitive polyketide moiety and the migration of the labile lactone.
Enantioselective synthesis of the core of banyaside, suomilide, and spumigin HKVV
Schindler, Corinna S.,Stephenson, Corey R. J.,Carreira, Erick M.
supporting information; experimental part, p. 8852 - 8855 (2009/05/30)
Concise: The first synthesis of the unique azabicyclononane core found in the aeruginosin class of serine protease inhibitors is described. The route is characterized by its efficiency (eight steps) and sets the stage for subsequent introduction of the gl
