A highly enantioselective total synthesis of (+)-goniodiol.
A high-yielding enantioselective total synthesis of the bioactive styryllactone (+)-goniodiol has been realised, starting from readily available (S)-glycidol. A key step is an oxygen-to-carbon rearrangement of a silyl enol ether linked via an anomeric centre, facilitating the rapid and diastereoselective construction of this functionalised system.
Tate
Edward W
EW
Biological and Biophysical Chemistry Section, Department of Chemistry, Imperial College London, UK. e.tate@imperial.ac.uk
Dixon
Darren J
DJ
Ley
Steven V
SV
D004852:Epoxy Compounds / Q000737:chemistry; D004986:Ether; D007783:Lactones / Q000138:chemical synthesis; D020005:Propanols / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D004852:Epoxy Compounds; D007783:Lactones; D020005:Propanols; D011753:Pyrones; C446739:goniodiol; D004986:Ether; C004312:glycidol