342008-05-3

Upstream product

• 342007-88-9 4-((2S,3S,4R)-3,4-Bis-benzyloxy-5-oxo-pyrrolidin-2-yl)-butyraldehyde 
• 100-39-0 benzyl bromide 
• 342008-01-9 (3R,4S,5S)-3,4-Dihydroxy-1-(4-methoxy-benzyl)-5-pent-4-enyl-pyrrolidin-2-one 
• 342007-87-8 (3R,4S,5S)-3,4-Bis-benzyloxy-1-(4-methoxy-benzyl)-5-pent-4-enyl-pyrrolidin-2-one 

Downstream Products

• 342007-89-0 (1S,2R,8aS)-1,2-Bis-benzyloxy-hexahydro-indolizin-3-one 
• 161024-43-7 (+)-lentiginosine 

Relevant academic research and scientific papers

SmI2-mediated hetero-coupling reaction of lactams with aldehydes; synthesis of indolizidine alkaloids, (-)-δ-coniceine, (+)-5-epiindolizidine 167B and (+)-lentiginosine

Treatment of alicyclic and aromatic lactams with several aldehydes in the presence of samarium(II) diiodide was found to undergo a novel nitrogen-carbon (hetero) coupling reaction to generate N-α-hydroxyalkylated lactams in high yield. The chiral lactams with an aldehyde-side chain incorporating the L-pyroglutamic acid- or L-tartaric acid-derived skeleton also reacted intramolecularly under the same conditions to afford the corresponding bicyclic coupling products, which were further applied to the convenient syntheses of (-)-δ-coniceine, (+)-5-epiindolizidine 167B and (+)-lentiginosine, respectively.