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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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Supplementary files

Article information


Submitted
08 Aug 2014
Accepted
16 Sep 2014
First published
18 Sep 2014

This article is Open Access

Chem. Commun., 2014,50, 13725-13728
Article type
Communication
Author version available

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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