en
Scientific article
Letter
English

The Enantiospecific Synthesis of (-)-Monomorine from L-Glutamic Ester

Published inTetrahedron Letters, vol. 35, no. 27, p. 4759-4762
Publication date1994
Abstract

Diethyl L-glutamate hydrochloride (3) was converted to its N-pyrrole derivative 5. Submission of 5 to butyryl chloride in boiling toluene gave the 2-butyryl derivative, and by treatment with NaBH₃CN and ZnI₂, the 2-butyl analogue 9. Cyclization of 9 with BBr₃ afforded (5S)-3-butyl-5-ethoxycarbonyl-5,6-dihydro-8(7H)-indolizinone (10). Hydrogenation of 10 over Pd/C in acidified EtOH gave (3S,5S,9R)-3-butyl-5-ethoxycarbonylindolizidine. By successive reduction of the latter to the primary alcohol, formation of the chloride and reductive dechlorination with tributyltin hydride, (3S,5R,9R)-3-butyl-5-methylindolizidine, or (-)-monomorine, was obtained in 8 steps from 3 in a yield of 25%.

Keywords
  • Pyrrole
  • Intramolecular acylation
  • Catalytic hydrogenation
  • 3.5-Disubstituted indolizidine
Funding
  • Swiss National Science Foundation - 20-32'166.91
Citation (ISO format)
JEFFORD, Charles, SIENKIEWICZ, Krzysztof, THORNTON, Steven Rupert. The Enantiospecific Synthesis of (-)-Monomorine from L-Glutamic Ester. In: Tetrahedron Letters, 1994, vol. 35, n° 27, p. 4759–4762. doi: 10.1016/S0040-4039(00)76960-7
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ISSN of the journal0040-4039
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