2-Furyl)ethanol ( 6) has been converted into methyl (f)-daunosaminide ( I ) and methyl ( ) -ristosaminide (3) by use of an intramolecular cyclisation of a trichloroacetimidate group. ( f ) -Daunosamine (1 ) has been obtained more directly from the alcohol (1 0) by use of a modified Mitsunobu reaction; the scope of the latter reaction has been explored using cyclohex-2-en-l -ol as a model substrate.Asymmetric reduction of 2-acetylfuran (5) has given (S)-I -(2-fury1)ethanol (46) in good enantiomeric excess, thus providing a short route to the L-enantiomers of the amino sugars ( I ) , (2), and(3) from a cheap, non-carbohydrate precursor.
A method for the introduction of amino groups into aliphatic systems is described. Cyclohex-2-en01 reacts with aromatic diacylamines under Mitsunobu reaction conditions to give either N-alkylated or 0alkylated products in a controlled, predictable manner. The product cyclohexenes, with Nbromosuccinimide, give either 1,2or 1,3-neighbouring group participation leading to 1,2,3trisubstituted cyclohexanes. The adducts may be used to give a range of 1,2-and 1,3-amino alcohols in a stereocontrolled process.
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