Phenanthrene synthesis: the synthesis of juncunone and the micandrols-A, B, E, and F
Abstract
The synthesis of the naturally occurring phenanthrenes micandrol-A (1,7-dimethylphenanthrene-2,6-diol)(1), micandrol-B (9,10-dihydro-1,7-dimethylphenanthrene-2,6-diol)(2),micandrol-E (7-methoxy-1,2-dimethylphenanthren-6-ol)(3), micandrol-F (9,10-dihydro-7-methoxy-1,2-dimethylphenanthren-6-ol)(4), and juncunone [1-(9,10-dihydro-2,6-dihydroxy-1,7-dimethylphenanthren-5-yl)ethan-1-one](7), by a method involving cyclization of suitable (Z)-2-chlorostilbenes with activated magnesium, is described.