title: Studies towards the synthesis of halomon: asymmetric hexafunctionalisation of myrcene.
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.
authors.affiliation: Department of Chemistry, Imperial College London, London, SW7 2AZ, UK. c.braddock@imperial.ac.uk.
authors.forename: D Christopher
authors.initials: DC
authors.lastname: Braddock
authors.forename: Alison X
authors.initials: AX
authors.lastname: Gao
authors.forename: Andrew J P
authors.initials: AJ
authors.lastname: White
authors.forename: Mariko
authors.initials: M
authors.lastname: Whyte
mesh_terms: D000080462:Acyclic Monoterpenes; D000475:Alkenes / Q000737:chemistry*; D054879:Halogenation; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D006900:Hydroxylation; D039821:Monoterpenes / Q000737:chemistry*
chemical_list: D000080462:Acyclic Monoterpenes; D000475:Alkenes; D006846:Hydrocarbons, Halogenated; D039821:Monoterpenes; C076123:6-bromo-3-(bromomethyl)-7-methyl-2,3,7-trichloro-1-octene; C509595:myrcene