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Issue 89, 2014
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Studies towards the synthesis of halomon: asymmetric hexafunctionalisation of myrcene

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Abstract

A novel dihydroxylation–dibromination–dihydroxylation sequence employing in situ protection of diols as boronate esters during the dihydroxylation reactions provides the first enantiomerically pure hexafunctionalised myrcene derivative. This concise four-step asymmetric sequence provides an advanced intermediate for the targeted synthesis of halomon via stereospecific transformations, where both stereogenic centres of the natural product have been set.

Graphical abstract: Studies towards the synthesis of halomon: asymmetric hexafunctionalisation of myrcene

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Publication details

The article was received on 08 Aug 2014, accepted on 16 Sep 2014 and first published on 18 Sep 2014


Article type: Communication
DOI: 10.1039/C4CC06234E
Citation: Chem. Commun., 2014,50, 13725-13728
  • Open access: Creative Commons BY license
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    Studies towards the synthesis of halomon: asymmetric hexafunctionalisation of myrcene

    D. C. Braddock, A. X. Gao, A. J. P. White and M. Whyte, Chem. Commun., 2014, 50, 13725
    DOI: 10.1039/C4CC06234E

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