Synthesis of new diverse macrocycles from diol precursors

Charlotte Marie Madsen, Martin Hansen, Marie V. Thrane, Mads Hartvig Clausen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

The formation of a library of diverse macrocycles with different ring sizes from two easily accessible building blocks is presented. Reacting diol precursors with electrophilic reagents lead to 17-membered sulfites and 19-membered malonates in 34–79% yield. Double-reductive amination of dialdehyde analogs of the diol precursors leads to 15-membered amines in yields ranging from 9 to 60%, reflecting large differences in reactivity based on steric environment.
Original languageEnglish
JournalTetrahedron
Volume66
Issue number52
Pages (from-to)9849-9859
ISSN0040-4020
DOIs
Publication statusPublished - 2010

Keywords

  • Macrocyclization
  • Reductive amination
  • Diversity-oriented synthesis
  • Cyclic esters

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