Expedient total syntheses of rhein and diacerhein via Fries rearrangement

Steve Tisserand; Rachid Baati; Marc Nicolas; Charles Mioskowski

doi:10.1021/jo049228l

Expedient total syntheses of rhein and diacerhein via Fries rearrangement

J Org Chem. 2004 Dec 10;69(25):8982-3. doi: 10.1021/jo049228l.

Authors

Steve Tisserand¹, Rachid Baati, Marc Nicolas, Charles Mioskowski

Affiliation

¹ Université Louis Pasteur, Faculté de Pharmacie, UMR 7514, Laboratoire de Synthèse Bio-Organique, 74 route du Rhin, 67401 Illkirch-Graffenstaden, France.

PMID: 15575790
DOI: 10.1021/jo049228l

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anthraquinones / chemical synthesis*
Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
Molecular Structure

Substances

Anthraquinones
Anti-Inflammatory Agents, Non-Steroidal
diacerein
rhein