A unified strategy for the total synthesis of the angucycline antibiotics SF 2315A, urdamycinone B, and the shunt metabolite 104-2

Article abstract of DOI:10.1002/ijch.199700004

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 ring fusion oxygen functionality featured in SF 2315A (2) and SF 2315 B (3), (ii) preparation of C-glycosyl juglone 53, and (iii) NMO mediated oxidative aromatization of 60.