Journal article
Synthesis of naturally occurring iminosugars from D-fructose by the use of a zinc-mediated fragmentation reaction
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.
Language: | English |
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Publisher: | The Royal Society of Chemistry |
Year: | 2006 |
Pages: | 2898-2905 |
ISSN: | 14770539 and 14770520 |
Types: | Journal article |
DOI: | 10.1039/b605818c |
ORCIDs: | Madsen, Robert |