American Chemical Society
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Stereoselective Reactions of a (−)-Quinic Acid-Derived Enone:  Application to the Synthesis of the Core of Scyphostatin

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journal contribution
posted on 2003-05-08, 00:00 authored by Lynne M. Murray, Peter O'Brien, Richard J. K. Taylor
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.