Heterofunctionalized Cavitands by Macrocyclization of Sequence-Defined Foldamers

Org Lett. 2019 Oct 4;21(19):7763-7767. doi: 10.1021/acs.orglett.9b02708. Epub 2019 Sep 19.

Abstract

Macrocyclic hosts have long been the workhorses of molecular recognition. Despite the widespread use of container-shaped molecules as synthetic receptors, an efficient preparation of cavitands bearing multiple functional groups has not been realized. This Letter describes a new cavitand derived from a sequence-defined oligoamide foldamer scaffold. A solid-phase synthesis approach is reported, which enables the display of multiple chemically diverse functional groups on the cavitand rim.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Cyclization
  • Ethers, Cyclic / chemical synthesis*
  • Ethers, Cyclic / chemistry
  • Macrocyclic Compounds / chemical synthesis*
  • Macrocyclic Compounds / chemistry
  • Molecular Structure
  • Resorcinols / chemical synthesis*
  • Resorcinols / chemistry
  • Solid-Phase Synthesis Techniques

Substances

  • Ethers, Cyclic
  • Macrocyclic Compounds
  • Resorcinols
  • cavitand