Oxetanes from the Ring Contraction of ?-Triflates of ?-Lactones: Oxetane Nucleosides and Oxetane Amino Acids

Authors

  • Sarah F. Jenkinson Chemistry Research Laboratory Department of Chemistry University of Oxford Mansfield Road Oxford, OX13TA, UK;
  • George w. J. Fleet Chemistry Research Laboratory Department of Chemistry University of Oxford Mansfield Road Oxford, OX13TA, UK;, Email: george.fleet@chem.ox.ac.uk

DOI:

https://doi.org/10.2533/chimia.2011.71

Keywords:

Lactones, Nucleoside, Oxetane, Oxetanocin, Oxetin, Ring contraction, Sugar amino acid

Abstract

?-Triflates of ?-lactones with potassium carbonate in methanol give efficient contraction of the ring to oxetane-1-carboxylates in which the oxygen substituent at C(3) of the oxetane is predominantly trans to the carboxylate at C(2), regardless of the stereochemistry of the starting triflate. The limitations of the procedure are discussed and compared with analogous reactions for the preparation of THF carboxylates. The potential of the contraction in the preparation of oxetane nucleosides (such as oxetanocin) and oxetane sugar amino acids (analogues of oxetin) as peptidomimetics with predisposition to form secondary structural motifs is illustrated.

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Published

2011-02-23

Issue

Section

Scientific Articles

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