SYNTHESIS OF AMINO SUGARS VIA ISOXAZOLINES. NITRILE OXIDE-FURAN ADDUCTS AS KEY INTERMEDIATES IN THE ISOXAZOLINE ROUTE TOWARDS NOVEL AMINO SUGAR DERIVATIVES
New variations for 1,3-dipolar nitrile oxide cycloadditions to reluctant dipolarophiles furan and 2-methylfuran are presented.The furoisoxazoline adducts 6 and 7 are shown to represent highly advanced, yet versatile precursors for derivatives of novel C6 and C7 amino sugar derivatives, accessible by subsequent highly stereoselective modification (addition of HO/OCH3 or HO/OH) and/or LiAlH4 reduction.
Jaeger, Volker,Mueller, Ingrid
p. 3519 - 3528
(2007/10/02)
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