Expedient total syntheses of rhein and diacerhein via Fries rearrangement

…, R Baati, M Nicolas, C Mioskowski

Index: Tisserand, Steve; Baati, Rachid; Nicolas, Marc; Mioskowski, Charles Journal of Organic Chemistry, 2004 , vol. 69, # 25 p. 8982 - 8983

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Citation Number: 24

Abstract

Isolated in the free state and as the glucoside in Rheum polygonaceae species (rhubarb), Senna leaves, and several species of Cassia (Peguminosae), 1 rhein (1, Figure 1) is well-known for its applications in antiarthritic drugs. 2 Indeed, rhein is recognized to be the active metabolite of diacerhein (2), which inhibits interleukin-1 activity by reducing the collagenase production in articular cartilage. ... Figure 1 Structure of rhein (1), diacerhein (2), aloe-emodin (3), ...