339307-12-9

Upstream product

• 339307-04-9 methyl (1R,4aR,10aR)-6-benzamido-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate 
• 339307-00-5 methyl (1R,4aR,10aR)-1,4a-dimethyl-6-nitro-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylate 
• 339307-09-4 methyl (1R,4aR,10aR)-6-benzamido-1,4a-dimethyl-7-nitro-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate 
• 339307-02-7 methyl (1R,4aR,10aR)-6-amino-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylate 
• 1686-43-7 methyl (1R,4aR,10aR)-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylate 
• 98-88-4 benzoyl chloride 
• 1235-74-1 Methyl dehydroabietate 

Relevant academic research and scientific papers

A short synthesis of phenanthro[2,3-d]imidazoles from dehydroabietic acid. Application of the methodology as a convenient route to benzimidazoles

Methyl cis-deisopropyldehydroabietate was selectively nitrated at the 12-position by reaction with 'claycop', a montmorillonite clay impregnated with copper(II) nitrate. The 12-nitro compound was reduced to the corresponding amine and this was subjected to a combined acylation and ortho nitration. The compounds so produced were further converted into octahydro-1H-phenanthro[2,3-d]imidazoles by reductive cyclization. The same acylation-ortho nitration methodology was shown to provide a short synthesis of 2-substituted benzimidazoles from aniline.