Aldehyde-selective Wacker oxidation in a thiyl-mediated vinyl group transfer route to daunosamine.
[reaction: see text] 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.
Friestad
Gregory K
GK
Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA. gregory-friestad@uiowa.edu
Jiang
Tao
T
Mathies
Alex K
AK