Synthesis of naturally occurring iminosugars from D-fructose by the use of a zinc-mediated fragmentation reaction

Anne Lauritsen, Robert Madsen

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A short synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol (DAB) and a formal synthesis of australine are described. In both cases, D-fructose is employed as the starting material and converted into a protected methyl 6-deoxy-6-iodo-furanoside. Zinc-mediated fragmentation produces an unsaturated ketone which serves as a key building block for both syntheses. Ozonolysis, reductive amination with benzylamine and deprotection affordfs 1,4-dideoxy-1,4-imino-D-arabinitol in only 7 steps and 11% overall yield from D-fructose. Alternatively, reductive amination with homoallylamine, ring-closing metathesis and protecting group manipulations give rise to an intermediate which can be converted into australine in 3 steps. The intermediate is prepared by two different strategies both of which use a total of 9 steps. The first strategy utilizes benzyl ethers for protection of fructose while the second and more effective strategy employs an isopropylidene acetal.
Original languageEnglish
JournalOrganic & Biomolecular Chemistry
Issue number15
Pages (from-to)2898-2905
Publication statusPublished - 2006

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