Expedient total syntheses of rhein and diacerhein via Fries rearrangement.
Short and practical total syntheses of rhein (1) and diacerhein (2) have been achieved via a Fries rearrangement and bis-carbonylation strategy followed by cyclization in molten salt, starting from dibromoester 7.
Tisserand
Steve
S
Université Louis Pasteur, Faculté de Pharmacie, UMR 7514, Laboratoire de Synthèse Bio-Organique, 74 route du Rhin, 67401 Illkirch-Graffenstaden, France.
Baati
Rachid
R
Nicolas
Marc
M
Mioskowski
Charles
C
D000880:Anthraquinones / Q000138:chemical synthesis*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis*; D015394:Molecular Structure
D000880:Anthraquinones; D000894:Anti-Inflammatory Agents, Non-Steroidal; C025292:diacerein; C020491:rhein