Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

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Chemical Compound Review:

Australine (1R,3R,8R)-3-(hydroxymethyl)- 2,3,5,6,7,8...

Synonyms: AG-K-85013, NSC-637204, CTK7J7047, NSC637204, AC1L7V0D

Pearson, W.H. et al., Lauritsen, A. et al.

Pearson, Hines,

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High impact information on Australine

Three approaches were examined for the synthesis of 3-(hydroxymethyl)pyrrolizidines, a class of compounds that includes the polyhydroxylated pyrrolizidine alkaloids alexine (1), australine (2), and various stereoisomers of thereof [1].
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 [2].

References

Total syntheses of (+)-australine and (-)-7-epialexine. Pearson, W.H., Hines, J.V. J. Org. Chem. (2000) [Pubmed]
Synthesis of naturally occurring iminosugars from D-fructose by the use of a zinc-mediated fragmentation reaction. Lauritsen, A., Madsen, R. Org. Biomol. Chem. (2006) [Pubmed]

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