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Biomimetic Synthesis of Hitorins A and B via an Intermolecular Alkoxy Radical-Olefin Coupling Cascade

A biomimetic synthesis of hitorins A and B was
achieved based on our modified biosynthetic proposal. In our synthesis, a
radical cascade reaction between an alkoxy radical, generated from a
hydroperoxide, and a monoterpene (+)-sabinene renders the tetrahydrofuran ring
of hitorins A and B. In addition, experimental results supported that the
oxidative cleavage of the tetrasubstituted olefin in a key intermediate is via
a radical oxidation cascade followed by a Grob fragmentation.