Synthesis of cyclic dimeric methyl morpholinoside - A common synthetic precursor to cyclic dinucleotide analogs

Charles R. Kinzie, Andrew D. Steele, Stacy M. Pasciolla, William M. Wuest*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

An eight-step synthesis of cyclic dimeric methyl morpholinoside (c-di-MM), a common synthetic precursor to a number of cyclic dinucleotide analogs is reported. The synthesis of c-di-MM proceeds through a morpholine monomer prepared from readily available inexpensive starting materials and culminates with a key macrolactamization reaction to provide the macrocycle in 15% overall yield.

Original languageEnglish
Pages (from-to)4966-4968
Number of pages3
JournalTetrahedron Letters
Volume55
Issue number35
DOIs
Publication statusPublished - 2014
Externally publishedYes

Keywords

  • Morpholine
  • Second messenger molecule
  • Signaling nucleotide
  • c-di-AMP
  • c-di-GMP

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