Revision of the structure of cuculoquinone to 3,3′-bis(6-ethyl-2,5,7,8-tetrahydroxy-1,4-naphthoquinone) and confirmation of the proposed structure by synthesis

• Published in: Tetrahedron letters Vol. 52; no. 28; pp. 3651 - 3653
• Main Authors: Pokhilo, Nataly D., Dragan, Sergey V., Anufriev, Victor Ph
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 13-07-2011; Elsevier
• Subjects: 3,3′-Bis(6-ethyl-2,5,7,8-tetrahydroxy-1,4-naphthoquinone); 3,3′-Bis(6-ethyl-2,7-dihydroxynaphthazarin); 3,3′-Bis(7-ethyl-2,5,6,8-tetrahydroxy-1,4-naphthoquinone); 3,3′-Bis(7-ethyl-2,6-dihydroxynaphthazarin); Cetraria cucullata; Cuculoquinone; Lichens; Synthesis (chemistry); Tetrahedrons; 3,3′-Bis(7-ethyl-2,6-dihydroxynaphthazarin); 3,3′-Bis(7-ethyl-2,5,6,8-tetrahydroxy-1,4-naphthoquinone); Cetraria cucullata; 3,3′-Bis(6-ethyl-2,5,7,8-tetrahydroxy-1,4-naphthoquinone); 3,3′-Bis(6-ethyl-2,7-dihydroxynaphthazarin); Cuculoquinone
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2011.05.026

A reinvestigation of cuculoquinone, previously isolated from the lichen Cetraria cucullata, led to a revision of the proposed structure to 3,3′-bis(6-ethyl-2,5,7,8-tetrahydroxy-1,4-naphthoquinone). The new structure was confirmed by synthesis.