712016-55-2

Upstream product

• 37597-19-6 1‐(3,4‐dimethoxyphenethyl)‐1H‐pyrrole‐2,5‐dione 
• 446063-58-7 (-)-[(1S,2R,4R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]-1-yl)methylsulfanyl]-N-[2-(3,4-dimethoxyphenyl)ethyl]maleimide 
• 446063-57-6 (-)-[(1S,2R,4R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]-1-yl)methylsulfanyl]-N-[2-(3,4-dimethoxyphenyl)ethyl]succinimide 
• 446063-56-5 (2R,6S)-4-[2-(3,4-dimethoxyphenyl)ethyl]-2-[(1S,2R,4R,S_R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methylsulfinyl]-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 

Relevant academic research and scientific papers

Enantiodivergent synthesis of pyrrolo[2,1-α]isoquinolines based on diastereoselective parham cyclization and α-amidoalkylation reactions

Enantiodivergent synthesis of C-10b-substituted pyrrolo[2,1-α ]isoquinolines starting from an enantiomerically pure N-phenethylnorborn-5-en-endo-2,3-dicarboxyimide 3a, with a 2-exo-hydroxy-10-bornylsulfinyl group as a chiral auxiliary, has been developed. The key transformations are derived from diastereoselective intramolecular cyclization of aryllithiums and α-amidoalkylation reactions, with the ethylidene bridge of the norbornene moiety dictating the stereochemical outcome in both types of reactions. Thus, the organolithium addition-intramolecular α-amidoalkylation sequence on imide 3a afforded stereoselectively the R configuration at C-12b, whereas the tandem Parham cyclization-intermolecular α-amidoalkylation reactions on the corresponding iodinated imide 3b occurred with complete control of stereoselectivity, leading to the epimer at C-12b. Subsequent reductive removal of the chiral auxiliary and retro-Diels-Alder reaction afforded (10bS)-and (10bR)-pyrroloisoquinolines 1 in high yields and optical purities (>99% ee).