en
Scientific article
Letter
English

Enantiospecific Syntheses of Indolizidines 167B and 209D

Published inTetrahedron Letters, vol. 34, no. 19, p. 3119-3122
Publication date1993
Abstract

Indolizidine 209D (2) was synthesized in 11 steps from L-aspartic acid (3) in an overall yield of 16%. 3R-pyrrolylnonanoic acid, prepared from 3, was converted into the α-keto diazomethyl derivative, which on Rh₂ (OAc)₄₋ catalyzed cyclization and catalytic hydrogenation gave 2. A similar procedure, starting from 3, afforded 3R-pyrrolylhexanoic acid, an intermediate which had previously been converted in 3 steps to indolizidine 167B.

Keywords
  • β-Amino acid
  • Pyrrole
  • Rhodium acetate
  • Catalytic hydrogenation
Funding
  • Swiss National Science Foundation - 20-32'166.91
Citation (ISO format)
JEFFORD, Charles, WANG, Jian Bo. Enantiospecific Syntheses of Indolizidines 167B and 209D. In: Tetrahedron Letters, 1993, vol. 34, n° 19, p. 3119–3122. doi: 10.1016/S0040-4039(00)93394-X
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Article (Published version)
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Identifiers
ISSN of the journal0040-4039
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