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

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Resolution of an iridoid synthon, gastrolactol, by means of dynamic acetylation and lipase-catalyzed alcoholysis.

A short synthetic route to asymmetric iridoids was developed. The three key steps were an intramolecular [4 + 2] cycloaddition reaction of an enamine derivative of 8-oxocitral (2), a dynamic acetylation, and an enzymatic resolution of the gastrolactyl acetates 5a and 5b, iridoids with three stereocenters. Some regio- and stereoselective heterogeneous catalytic hydrogenations of double bonds in iridoid aglucones were discussed.[1]

References

  1. Resolution of an iridoid synthon, gastrolactol, by means of dynamic acetylation and lipase-catalyzed alcoholysis. Santangelo, E.M., Rotticci, D., Liblikas, I., Norin, T., Unelius, C.R. J. Org. Chem. (2001) [Pubmed]
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