212902-41-5

Upstream product

• 159593-22-3 diethyl (2S,3S)-2,3-di-O-methoxymethyl-tartrate 
• 166734-76-5 (2R,3R)-2,3-bis(methoxymethoxy)butane-1,4-diol 
• 100-46-9 benzylamine 
• 212902-39-1 1,4-di-O-methanesulfonyl-2,3-di-O-(methoxymethyl)-D-threitol 

Downstream Products

• 212902-55-1 (2R,3aR,4R,5R)-hexahydro-2-benzyloxycarbonylmethyl-4,5-bis(methoxymethoxy)pyrrolo[1,2-b]isoxazole 
• 212967-34-5 (2S,3aR,4R,5R)-hexahydro-2-t-butyldiphenylsilyloxymethyl-4,5-bis(methoxymethoxy)-pyrrolo[1,2-b]isoxazole 

Relevant academic research and scientific papers

Synthesis of trihydroxylated pyrrolizidines and indolizidines using cycloaddition reactions of functionalized cyclic nitrones, and the synthesis of (+)- and (-)-lentiginosine

Cycloadditions of 3,4-isopropylidenedioxy-Δ1-pyrroline-1-oxide (9), (3S,4S)-3,4-bis(methoxy-methoxy)-Δ1-pyrroline-N-oxide (28), and its (3R, 4R)-enantiomer, with suitably-functionalized alkenes has led to the synthesis of the 1,2,6-trihydroxypyrrolizidines 14, 33 and ent-33, and the 1,2,7- trihydroxyindolizidines 22, 39 and ent-39. Deoxygenation of two enantiomeric intermediates in these syntheses led to the preparation of the dihydroxylated indolizidine (+)-lentiginosine and its (-)-enantiomer.