Aromatic molecules are key constituents of many pharmaceuticals, electronic materials, and commodity plastics. The utility of these molecules directly reflects the identity and pattern of substituents on the aromatic ring. Here, we report a palladium(II) catalyst system, incorporating an unconventional ortho-dimethylaminopyridine ligand, for the conversion of substituted cyclohexanones to the corresponding phenols. The reaction proceeds via successive dehydrogenation of two saturated carbon-carbon bonds of the six-membered ring and uses molecular oxygen as the hydrogen acceptor. This reactivity demonstrates a versatile and efficient strategy for the synthesis of substituted aromatic molecules with fundamentally different selectivity constraints from the numerous known synthetic methods that rely on substitution of a preexisting aromatic ring.

/pdf/palladium-catalyzed-aerobic-dehydrogenation-of-substituted-47sjwnxu0m.pdf

Palladium-Catalyzed Aerobic Dehydrogenation of Substituted Cyclohexanones to Phenols

Synthesis of cicerfuran, an antifungal benzofuran, and some related analogues

A Formal [3 + 3] Cycloaddition Approach to Natural-Product Synthesis

A series of disubstituted 3‘,4‘-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) analogues (1−10) were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. 5-Methoxy-4-methyl DCK (8) was the most promising compound with an EC50 value of 7.21 × 10-6 μM and a therapeutic index of >2.08 × 10,7 which were much better than those of lead compound DCK in the same assay. Another six disubstituted DCK analogues (1−5 and 7) were more potent than AZT but less active than DCK. Conformational analysis suggested that resonance of the coumarin system is an essential structural feature for potent anti-HIV activity. Steric compression of C(4) and C(5) substituents of the coumarin moiety can reduce the overall planarity and thus resonance of the coumarin nucleus, resulting in a decrease or lack of anti-HIV activity.

Anti-AIDS agents. 42. Synthesis and anti-HIV activity of disubstituted (3'R,4'R)-3',4'-di-O-(S)-camphanoyl-(+)-cis-khellactone analogues.

Natural phenolic compounds 1900-2000: a bird's eye view of a century's chemistry.

Syntheses a partir du chlorure d'acide benzodioxole-1,3acetique-5 (ou de son derive methoxy-6) et de dimethyl-2,2 chromannol-3, resorcinol ou isoprenyloxy-3 phenol

Total synthesis of isoflavones: jamaicin, calopogonium isoflavone-B, pseudobaptigenin, and maxima substance-B. Friedel-Crafts acylation reactions with acid-sensitive substrates

William A. Price

Papers

Total synthesis of isoflavones: jamaicin, calopogonium isoflavone-B, pseudobaptigenin, and maxima substance-B. Friedel-Crafts acylation reactions with acid-sensitive substrates

Mild, efficient trimethylaluminum-mediated cyclopropanations. An innovative synthesis of the new dehydrogenase inhibitor spiropentaneacetic acid

Mild, Efficient Trimethylaluminum-Mediated Cyclopropanations. An Innovative Synthesis of the New Dehydrogenase Inhibitor Spiropentaneacetic Acid.