The first synthetically useful interrupted Witkop oxidation has been disclosed through a radical triggered oxidative peroxycyclization of tryptamine derivatives, using a TBAI/TBHP catalytic system. This differs from known tryptophan oxidations, which typically cleave the 2,3-double bond. Upon one-pot reduction, this system renders an easy access to structurally distinct peroxypyrroloindoles, which are demonstrated to be useful precursors in various downstream synthetic elaborations.
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The first synthetically useful interrupted Witkop oxidation has been disclosed through a radical triggered oxidative peroxycyclization of tryptamine derivatives, using a TBAI/TBHP catalytic system. This differs from known tryptophan oxidations, which typically cleave the 2,3-double bond. Upon one-pot reduction, this system renders an easy access to structurally distinct peroxypyrroloindoles, which are demonstrated to be useful precursors in various downstream synthetic elaborations.
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