A divergent entry to 1,2,3,9-tetrahydroxyquinolizidines

Takuya Okada*, Takanori Ozaki, Atsushi Kato, Isao Adachi, Naoki Toyooka*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Polyhydroxylated quinolizidines should be expected to show high inhibitory activity for glycosidases, similar to other polyhydroxylated nitrogen-containing heterocycles, however, very few investigations into the synthesis and biological evaluations of polyhydroxylated quinolizidines have been reported. We achieved the enantiodivergent synthesis of polyhydroxylated quinolizidines (1S, 2S, 3S, 9S, 9aR)-1,2,3,9-tetrahydroxyquinolizidine 8 and its enantiomer starting from the key intermediate (5S, 6S)-1-allyl-6-((R)-1-hydroxyallyl)-5-(methoxymethoxy)piperidin-2-one 7 via (1S, 9R, 9aS)-9-hydroxy-1-(methoxymethoxy)-2, 3, 9, 9a-tetrahydro-1H-quinolizin-4(6H)-one 13 having the pseudo-symmetry. In addition, two diastereomeric quinolizidines (1R, 2S, 3S, 9S, 9aR)-1,2,3,9-tetrahydroxyquinolizidine 9 and (1R, 2R, 3R, 9S, 9aR)-1,2,3,9-tetrahydroxyquinolizidine 10 were also synthesized from common intermediate 7.

Original languageEnglish
Article number152030
JournalTetrahedron Letters
Volume61
Issue number25
DOIs
StatePublished - 2020/06/18

Keywords

  • Chiral building block
  • Enantiodivergent synthesis
  • Glycosidase
  • Polyhydroxylated quinolizidine
  • Pseudo-symmetry

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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