1187560-41-3Relevant articles and documents
Polyol synthesis with β-Oxyanionic alkyllithium Reagents: Syntheses of aculeatins A, B, and D
Malathong, Viengkham,Rychnovsky, Scott D.
scheme or table, p. 4220 - 4223 (2009/12/31)
Synthesis of ketone aldol products using a non-aldol route was developed. The β-phenylthio alcohols were prepared from optically pure oxiranes. Deprotonation and reductive lithiation generated the key intermediate, a β-oxyanionic alkyllithium reagent. Addition to a Weinreb amide produced the β-hydroxy ketone In >90% yield using only 1.5 equiv of the phenylthio alcohol. Stereoselective reduction of the ketone led to either the syn-or anti-1,3-diol. This simple, convergent sequence was used to prepare aculeatins A, B, and D from a common intermediate