Abstract The first total synthesis of the proposed structure of δ-indomycinone has been accomplished. The key steps involve the Diels–Alder reaction of a bromonaphthoquinone (6) and 1-methoxy-3-methyl-1-trimethylsiloxy-1, 3-butadiene (7) to access the anthraquinone skeleton, representing a common building block of other naturally occurring anthraquinone antibiotics, regioselective bromination of anthraquinone (14) and a highly ...