466645-80-7

Upstream product

• 466645-77-2 Acetic acid (1S,4S,6S)-4-[allyl-(4-nitro-benzenesulfonyl)-amino]-6-(tert-butyl-dimethyl-silanyloxy)-cyclohept-2-enyl ester 
• 134734-52-4 (1R,4S,6S)-4-acetoxy-6-[(tert-butyldimethylsilyl)oxy]-2-cyclohepten-1-ol 
• 100704-44-7 N-allyl-p-nitrobenzenesulfonamide 
• 466645-79-4 N-allyl-N-[6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohept-2-enyl]-4-nitro-benzenesulfonamide 

Downstream Products

• 46727-05-3 1,3-bis-(1-methyl-pyrrolidin-2-yl)-propan-2-one 
• 468732-35-6 dihydrocuscohydrine 
• 466645-81-8 N-allyl-N-[4-allylamino-6-(tert-butyl-dimethyl-silanyloxy)-cyclohept-2-enyl]-4-nitro-benzenesulfonamide 

Relevant academic research and scientific papers

Total synthesis of (+)-dihydrocuscohygrine and cuscohygrine

The first enantioselective synthesis of (+)-dihydrocuscohygrine 1 and cuscohygrine 2 is presented. 1 was obtained in nine steps and 30% overall yield with a ruthenium-catalyzed tandem ring rearrangement metathesis key step starting from enantiomerically pure cycloheptene-1,3,5-triol derivative 6. The unknown absolute configuration of natural dihydrocuscohygrine 1 could be determined as (S,S)-(-). Cuscohygrine 2 was obtained by Jones oxidation of 1 in quantitative yield but unfortunately with complete epimerization.