Synthesis of trihydroxylated pyrrolizidines and indolizidines using cycloaddition reactions of functionalized cyclic nitrones, and the synthesis of (+)- and (-)-lentiginosine

Avril E. McCaig, Kevin P. Meldrum, Richard H. Wightman

Research output: Contribution to journalArticle

104 Citations (Scopus)

Abstract

Cycloadditions of 3,4-isopropylidenedioxy-?1-pyrroline-1-oxide (9), (3S,4S)-3,4-bis(methoxy-methoxy)-?1-pyrroline-N-oxide (28), and its (3R, 4R)-enantiomer, with suitably-functionalized alkenes has led to the synthesis of the 1,2,6-trihydroxypyrrolizidines 14, 33 and ent-33, and the 1,2,7- trihydroxyindolizidines 22, 39 and ent-39. Deoxygenation of two enantiomeric intermediates in these syntheses led to the preparation of the dihydroxylated indolizidine (+)-lentiginosine and its (-)-enantiomer.

Original languageEnglish
Pages (from-to)9429-9446
Number of pages18
JournalTetrahedron
Volume54
Issue number32
DOIs
Publication statusPublished - 6 Aug 1998

Keywords

  • Alkaloids
  • Cycloadditions
  • Indolizidines
  • Pyrrolizidines

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