Rapid Biomimetic Total Synthesis of (±)-Rossinone B.

A biomimetic total synthesis of (±)-rossinone B has been achieved through a highly efficient strategy featuring a series of rationally designed reactions, including a one-pot allylic rearrangement/oxidation reaction to generate the vinyl quinone 27, an intramolecular vinyl quinone Diels−Alder reaction to construct the linear 6−6−5 tricyclic core of 28, and a double conjugate addition/β-elimination cascade to complete the total synthesis of 1. [ABSTRACT FROM AUTHOR]