Versatile 8-oxabicyclo[3.2.1]oct-6-en-3-one: stereoselective methodology for generating C-glycosides, delta-valerolactones, and polyacetate segments

Org Lett. 2001 Jan 25;3(2):177-80. doi: 10.1021/ol006737a.

Abstract

[figure: see text] A new rearrangement of functionalized methoxy glycosides and a regioselective as well as stereoselective intramolecular Michael addition giving delta-valerolactones and C-glycosides are described. Applications to the synthesis of marine natural products are reported. Chemoselective deprotection of benzylated hydroxy groups is assumed to be facilitated by 6-endo-tet interaction with the 1,3-dithiane functionality.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemical synthesis*
  • Biological Factors / chemical synthesis*
  • Glycosides / chemical synthesis*
  • Indicators and Reagents
  • Lactones / chemical synthesis*
  • Molecular Structure
  • Seawater

Substances

  • Acetates
  • Biological Factors
  • Glycosides
  • Indicators and Reagents
  • Lactones
  • gamma-valerolactone