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Synthesis of 2,3-Dihydro-7-hydroxymethyl-1H-pyrrolizin-1-one, the Alkaloid Loroquine

✍ Scribed by Röder, Erhard ;Bartkowski, Jan-Pit Barko ;Bourauel, Thomas

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
344 KB
Volume
1993
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

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 give loroquine (4) in 2.1% overall yield.

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