An efficient method for the synthesis of (1S,2R,4R,5S)- and
(-)-6 and (-)-9 and (1R,2R,3S,4R)- and (1S,2R,3S,4R)-2-amino-
3,4-dihydroxycyclohexanecarboxylic acids (-)-15 and (-)-18 was
developed by using the OsO4-catalyzed oxidation of Boc-protected
(1S,2R)-2-aminocyclohex-4-enecarboxylic acid (+)-2 and
(1R,2S)-2-aminocyclohex-3-ene-carboxylic acid (+)-11. Good
yields were obtained. The stereochemistry of the synthesized
compounds was proven by NMR spectroscopy. (C) 2009 Elsevier Ltd.
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