Stereoselective reactions of a (-)-quinic acid-derived enone: application to the synthesis of the core of scyphostatin.
[reaction: see text] A (-)-quinic acid-derived enone, with the trans-1,2-diol protected as a 2,3-dimethoxybutanediyldioxy ketal, provides an excellent template for further highly stereoselective elaboration as exemplified by its conversion into the core of scyphostatin, a potent inhibitor of neutral sphingomyelinase.
Murray
Lynne M
LM
Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.
O'Brien
Peter
P
Taylor
Richard J K
RJ
D000577:Amides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D011753:Pyrones / Q000138:chemical synthesis*; D011801:Quinic Acid / Q000737:chemistry*; D013108:Sphingomyelin Phosphodiesterase / Q000037:antagonists & inhibitors; D013237:Stereoisomerism
D000577:Amides; D007202:Indicators and Reagents; D011753:Pyrones; C121123:scyphostatin; D011801:Quinic Acid; D013108:Sphingomyelin Phosphodiesterase