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

作者信息

Friestad Gregory K, Jiang Tao, Mathies Alex K

机构信息

Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA.

出版信息

Org Lett. 2007 Mar 1;9(5):777-80. doi: 10.1021/ol063010z. Epub 2007 Feb 7.

Abstract

[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.

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