Regiospecific Synthesis of Dimethylphenanthrenes

Abstract

The dimethylated phenanthrenes 2,3-dimethylphenanthrene (4a), 2,7-dimethylphenan threne (4b), 2,6-dimethylphenanthrene (4c) and 1,7-dimethylphenanthrene (4d) have been prepared in gram-quantities by a short sequence of directed ortho metalation (DoM) of N,N-diethylbenzamides followed by Suzuki-Miyaura cross-coupling reaction and directed remote metalation (DreM) to form 9-phenanthrols. The final phenanthrenes were obtained through protection/deprotection as triflates.

Substituted Two- to Five-Ring Polycyclic Aromatic Compounds Are Potent Agonists of Atlantic Cod (Gadus morhua) Aryl Hydrocarbon Receptors Ahr1a and Ahr2a

“…The synthesis of (1R,2R)-1,2-dihydrophenanthrene-1,2-diol (R,R-1,2-DHP), 11 1-,2-,3-,4-methoxychrysene (1-,2-,3-,4-MOC) and chrysene-1-ol,-2-ol,-3-ol,-4-ol (1-,2-,3-,4-COH), 41 1-,2-,3-,4-,6-methylchrysene (1-,2-,3-,4-,6-MC), 42 3ethylphenanthrene (3-EP), and 3-propylphenanthrene (3-PP) 43 is described elsewhere. 1,7-, 2,3-, and 2,7-dimethylphenanthrene (1,7-, 2,3-, and 2,7-DMP) were prepared as described by Boḧme et al, 44 and the preparation of 2,3dimethoxychrysene (2,3-DMOC) is described in the Supporting Information. Transfection, Exposure, Luciferase Reporter Gene Assay, and Viability Assay.…”

Alkyl-phenanthrenes in early life stage fish: differential toxicity in Atlantic haddock (Melanogrammus aeglefinus) embryos

“…C2-compounds 1,7-DMP, 2,3-DMP and 2,7-DMP were resynthesized according to the procedures given by Böhme, et al 2017. 22 C2-compounds 1,4-DMP, 3,6-DMP, and 3-EP and the C3-compound 3-PP were made by photochemical cyclization of stilbenes. 23,24 Full experimental details and NMR spectra are given in ESI, Part II †…”

One-Pot Three-Component Synthesis of Phenanthrenes via Palladium-Catalyzed Catellani and Retro-Diels–Alder Reactions

“…2,3-Dimethylphenanthrene (4m). 23 Purification (column chromatography through silica gel, pure PE). White solid (30.1 mg, 73%).…”