A Unified Strategy for the Total Synthesis of the Angucycline Antibiotics SF 2315A, Urdamycinone B, and the Shunt Metabolite 104–2

…, VA Boyd, A Sobti, GA Sulikowski

Index: Kim, Kyungjin; Boyd, Vincent A.; Sobti, Aditya; Sulikowski, Gary A. Israel Journal of Chemistry, 1997 , vol. 37, # 1 p. 3 - 22

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Citation Number: 24

Abstract

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 ...