Abstract Total syntheses of the angucycline antibiotics SF 2315A (2), urdamycinone B (4), and the shunt metabolite 104–2 (5) are described, as well as an approach toward the synthesis of SF 2315B (3). All four syntheses feature a Diels–Alder cycloaddition between a bromojuglone derivative and an optically active diene (25a), the latter derived from (–)- quinic acid. Subsequent key transformations include (i) stereocontrolled introduction of ...
