Total synthesis of rodgersinol: a survey of the Cu(II)-mediated coupling of ortho-substituted phenols

Full details of studies directed toward the total synthesis of both enantiomers of rodgersinol are described. The key parts of our synthetic route to rodgersinol included the Cu(II)-mediated coupling of an arylboronic acid with an ortho-alkyl substituted phenol and regio- and stereoselective construction of the hydroxypropyl substituent, which avoided tedious protection/deprotection sequence.