First asymmetric synthesis of the cyclohexanone subunit of baconipyrones A and B. Revision of its structure
An asymmetric synthesis of the 3,5-dihydroxycyclohexanone subunit of baconipyrones A and B, as well as that of the hydroxydiketone subunit of baconipyrones C and D ((-)-(4S,6S)-4,6-dimethyl-5-hydroxynonan-3,7-dione), is described. Key steps include sulfur dioxide-induced additions of enoxysilanes to 1,3-dioxy-1,3-dienes, followed by retro-ene desulfitations (retro-ene elimination of SO2).
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Keywords: Bond-forming reaction ; stereoselective-synthesis ; polypropionate ; fragments ; 4-component synthesis ; stereogenic centers ; methyl sulfones ; naked sugars ; one-pot ; derivatives ; esters
EPFL, Lab Glycochem & Asymmet Synth, BCH, CH-1015 Lausanne, Switzerland.
Record created on 2005-11-09, modified on 2016-08-08