Ontology highlight
ABSTRACT:
SUBMITTER: Guo H
PROVIDER: S-EPMC2531217 | biostudies-literature | 2006 Apr
REPOSITORIES: biostudies-literature
Organic letters 20060401 8
[reaction: see text] The enantioselective syntheses of both enantiomers of the indolizidine natural product swainsonine have been achieved in 13 steps from furan. The indolizidine ring system is installed by a one-pot hydrogenolysis of both an azide and an O-Bn group along with an intramolecular reductive amination reaction. The asymmetry of swainsonine was introduced by Noyori reduction of an acylfuran. This route relies upon an Achmatowicz rearrangement, a diastereoselective palladium-catalyze ...[more]