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α-Hydroxyacids can be enantioselectively prepared by means of a two-step oxidation process, involving first the asymmetric dihydroxylation of a terminal alkene and subsequent oxidation with TEMPO/NaOCl/NaClO 2 in good to excellent yields. No fragmentation of the glycol intermediate was detected.
The preparation of 11-hydroxy-eudesmanolides with the stereochemistry found in the Umbelliferae family of plants is described. The decalin system of the eudesmane skeleton is produced by the addition of 5-methyl-2-furyllithium to 3-ethoxycyclohex-2-enone and acidic treatment of the resulting adduct. The stereochemistry of the decalones obtained by this method has been corrected. The α-hydroxy-γ-lactone...
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