276246-12-9

Upstream product

• 6850-57-3 2-methoxybenzylamine 
• 276246-09-4 C₂₅H₃₂O₉S₂ 
• 276246-08-3 (3aR,4R,5S,6aR)-3a,4-Bis-hydroxymethyl-2,2,5-trimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-ol 
• 196859-81-1 5,6:4',6'-di-O-isopropylidene-antirrhinoside 

Relevant academic research and scientific papers

Conversion of the iridoid glucoside antirrhinoside into 3- azabicyclo[3.3.0]octane building blocks

The iridoid glucoside antirrhinoside (1) was transformed into polysubstituted 3-azabicyclo[3.3.0]octanes 3, 12, and 13 in 4 to 5 steps. Ozonolysis of the diacetonide of 1 and of its 7-deoxy-derivative 8 afforded cyclopentanoids 2 and 10, respectively. Conditions for the selective conversion of 2 and 10 into the corresponding ditosylates 4 and 11 were investigated. Cyclization of 4 and 11 was achieved with benzylamine and 2- methoxybenzylamine to yield bicyclic pyrrolidines 3, 12, and 13. Additional building blocks 14 and 15 were obtained by selective deprotection of the N- benzyl and isopropylidene moieties in 12 and 13, respectively.