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.
Highlights
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
We have shown that either regioisomer of single enantiomer 1,2-bromotosylates of terminal aliphatic alkenes can generate single enantiomer bromonium ions that can be trapped with chloride anion to give enantiopure 1,2-chlorobromides.14a We have shown that Sharpless dihydroxylation[16] of a trisubstituted olefin provides access to single enantiomer bromohydrins via stereospecific epoxide formation[17] and bromide ring-opening,[18] where suitable subsequent activation leads to single enantiomer bromonium ions.14b,c With these considerations in mind, we have targeted dibromotetrol (3R,6S,7S)-3 as an advanced intermediate for the synthesis of enantiopure halomon starting from myrcene 2 (Scheme 2)
Summary
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.
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