316129-47-2

Upstream product

• 102860-22-0 2-phenylsulfonyl-1,3-cyclohexadiene 
• 873-55-2 sodium benzenesulfonate 
• 316129-46-1 3-(phenylsulfonyl)-8-[(4-methylphenyl)sulfonyl]-2-(1-nitroethyl)-8-azabicyclo[3.2.1]octane 
• 177980-54-0 3-(phenylsulfonyl)-8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]-2-octene 
• 148459-11-4 1-(phenylsulfonyl)bicyclo<4.1.0>hept-2-ene 

Downstream Products

• 316129-48-3 1-acetyl-8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]oct-2-ene 
• 316129-49-4 2-(2-methyl-1,3-dioxolan-2-yl)-8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]oct-2-ene 
• 137331-57-8 8-Methyl-2-(methylcarbonyl)-8-azabicyclo<3.2.1>oct-2-ene 

Relevant academic research and scientific papers

BF3-induced rearrangement of aziridino cyclopropanes derived from 2-phenylsulfonyl 1,3-dienes. Application to the total synthesis of (±)-ferruginine

Total synthesis of the alkaloid (±)-ferruginine (1) has been developed via the 2-phenylsulfonyl 1,3-diene approach. BF3-induced rearrangement of the N-protected cyclohexane aziridino cyclopropane 8, derived from its corresponding epoxy cyclopropane, afforded the desired tropane alkaloid skeleton 9 in good yield. Michael addition of nitroethane (as an acyl anion equivalent) and transformation of the nitro group of the adduct 10 to a keto function gave 11. Elimination of benzenesulfinic acid and subsequent replacement of the tosyl group by a methyl group afforded the title compound 1.