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Aldehyde-Selective Wacker Oxidation in a Thiyl-Mediated Vinyl Group Transfer Route to Daunosamine
Journal article   Peer reviewed

Aldehyde-Selective Wacker Oxidation in a Thiyl-Mediated Vinyl Group Transfer Route to Daunosamine

Gregory K Friestad, Tao Jiang and Alex K Mathies
Organic letters, Vol.9(5), pp.777-780
03/01/2007
DOI: 10.1021/ol063010z
PMID: 17284042

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Abstract

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.

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