Phenanthrene 3:8-dimethoxy-4.hydroxy

Synthese von 2,4-Dimethoxy-6-hydroxy-phenanthren und Konstitution des Or-chinols, by E. Hardegger, H. R. Biland, and H. Corrodi (28. Mitteilung, Welkstoffe und Antobiotika), Helv. Chim. Acta, 46 (1963) 1354-1360. 

Three novel phenanthrenes have been isolated from the wetland plant Juncus acutus. The structures of the novel phenanthrenes were established as 2-hydroxy-l,6-dimethyl-5-vinyl-phenanthrene (320), 2,7-dimethoxy-l,6-dimethyl-5-vinylphenanthrene (321) and 2-hydroxy-6-hydroxymethyl-l-methyl-5-vinyl-phenanthrene (322) [164, 165]. In spite of the great number of 9,10-dihydrophenanthrenes, only quite a small number of phenanthrenes have been reported until now as constituents of Juncaceae. 

Trimethoxyphenanthrene-5-carboxylic acid [vm] can be converted through the ester to the azide [ix], but attempts to degrade the latter to the 5-amino compound failed nitrogen was lost and the product was identified as the lactone [x] of 4-hydroxy-3 8-dimethoxy-phenanthrene-5-carboxylic acid [11]. 

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