152401-26-8Relevant articles and documents
Synthesis of 2,3-Dihydro-7-hydroxymethyl-1H-pyrrolizin-1-one, the Alkaloid Loroquine
Roeder, Erhard,Bartkowski, Jan-Pit Barko,Bourauel, Thomas
, p. 711 - 714 (2007/10/02)
The title compound 4 is synthesized in 8 steps by cyclization of N-tosylglycinate 5 with vinyl ketone 6.After elimination of water and sulfinic acid the pyrrolecarboxylate 9 is obtained which, on N-alkylation with ethyl acrylate, Dieckmann cyclization, saponification and decarboxylation, yields methylloroquine 12.The reaction with chlorotrimethylsilane/sulfuric acid in acetic anhydride and subsequent saponification gave loroquine (4) in 2.1 percent overall yiels.Key Words: Pheromones / Pyrrolizidine alkaloids / Pyrrolizine / Alkaloids