Israel Journal of Chemistry p. 3 - 22 (1997)
Update date:2022-08-03
Topics:
Kim, Kyungjin
Boyd, Vincent A.
Sobti, Aditya
Sulikowski, Gary A.
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.
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