ISSN:
0170-2041
Keywords:
Pheromones
;
Pyrrolizidine alkaloids
;
Pyrrolizines
;
Alkaloids
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1993199301116
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