78018-56-1Relevant articles and documents
Biomimetic synthesis of dimeric metabolite acremine g via a highly regioselective and stereoselective Diels-Alder reaction
Arkoudis, Elias,Lykakis, Ioannis N.,Gryparis, Charis,Stratakis, Manolis
supporting information; experimental part, p. 2988 - 2991 (2009/12/06)
The dimeric metabolite acremine G was synthesized featuring a highly regioselective and stereoselective Diels-Alder reaction between a TBS-protected hydroquinone diene and a structurally related alkenyl quinone. The major endo [4 + 2] adduct slowly transforms to acremine G by the atmospheric air under the deprotection conditions (in situ generated HF).
Pyridinium Chlorochromate Releases Quinones from Hydroquinone Silyl Ethers.
Willis, John P.,Gogins, Kitty A.,Miller, Larry L.
, p. 3215 - 3218 (2007/10/02)
The pyridinium chlorochromate oxidation of six bis(trimethylsilyl) and six bis(tert-butyldimethylsilyl) ethers of p-hydroquinones at room temperature in methylene chloride solution gave the corresponding quinones in 60-90percent yield.The bis(trimethylsilyl) ethers were slightly more reactive than the bis(tert-butyldimethylsilyl) ethers.High oxidation efficiency was indicated by a 1:1 molar stoichiometry; however, more convenient reaction times were obtained at a 2:1 molar ratio of pyridinium chlorochromate (PCC) to hydroquinone silyl ether.The mechanism is discussed based upon comparisons of relative reaction rates with electrochemical oxidation potentials.