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).


Published in:
Organic Letters, 6, 18, 3031-3034
Year:
2004
ISSN:
1523-7060
Keywords:
Note:
EPFL, Lab Glycochem & Asymmet Synth, BCH, CH-1015 Lausanne, Switzerland.
Other identifiers:
Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


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