Chemical Communications 2011-07-21

Stereospecificity in the Au-catalysed cyclisation of monoallylic diols. Synthesis of (+)-isoaltholactone.

William P Unsworth, Kiri Stevens, Scott G Lamont, Jeremy Robertson

Index: Chem. Commun. (Camb.) 47(27) , 7659-61, (2011)

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Abstract

We describe a concise synthesis of (+)-isoaltholactone via a Au-catalysed cyclisation of a monoallylic diol to form the tetrahydrofuranyl ring. Analogous cyclisations show that the stereochemical outcome is dictated by the stereochemistry of the diol substrate.