Abstract:
A total synthesis of the naturally occurring cyclohexenetetrol conduritol A from p-benzoquinone was achieved in four steps with total stereoselectivity in 55% overall yield. Hydroboration of the tetrabenzoate ester of conduritol A gave racemic proto-quercitol stereoselectively.
In a stereoselective nine step synthesis p-benzoquinone was also converted to an aminocyclitol precursor. This work featured a stereospecific vanadium catalysed epoxidation of an allylic alcohol to complete the sequence, which constituted a formal total synthesis of the aminocyclitol 3-O-demethylfortamine. Preliminary investigations were also made toward introducing chirality into this sequence by enantiotopic differentiation of symmetrical compounds.
An investigation into the potential of p-benzoquinone monoxime as an aminocyclitol precursor was also initiated.