An expeditious route towards pyranopyran sugar amino acids

GM Grotenbreg, AW Tuin, MD Witte, MA Leeuwenburgh, JH van Boom, GA van der Marel, HS Overkleeft, M Overhand*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

21 Citations (Scopus)

Abstract

The synthesis of two diastereoisomeric pyranopyran sugar amino acids, starting from (+)-D-3,4,6-tri-O-benzylglucal, is described. The key reaction sequence towards the bicyclic structure entails Petasis olefination followed by ring closing metathesis.

Original languageEnglish
Pages (from-to)904-906
Number of pages3
JournalSynlett
Issue number5
DOIs
Publication statusPublished - 3-Apr-2004
Externally publishedYes

Keywords

  • amino acids
  • bicyclic compounds
  • carbohydrates
  • pyranopyran
  • ring-closing metathesis
  • RING-CLOSING METATHESIS
  • CARBOHYDRATE-DERIVATIVES
  • CONFORMATIONAL-ANALYSIS
  • CYCLIC-PEPTIDES
  • DESIGN

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