Aldehyde-selective Wacker oxidation in a thiyl-mediated vinyl group transfer route to daunosamine

Abstract

(Chemical Equation Presented) Asymmetric dihydroxylation, thiyl radical mediated transfer of a silicon-tethered vinyl group to a hydrazone and an unconventional aldehyde-selective Wacker oxidation are sequenced for an efficient synthesis of methyl N-trifluoroacetyl-L-daunosaminide in 32% overall yield from crotonaldehyde. © 2007 American Chemical Society.