66958-61-0Relevant academic research and scientific papers
Quinones. Part 2. General Synthetic Routes to Quinone Derivatives with Modified Polyprenyl Side Chains and the Inhibitory Effects of these Quinones on the Generation of the Slow Reacting Substance of Anaphylaxis (SRS-A)
Terao, Shinji,Shiraishi, Mitsuru,Kato, Kaneyoshi,Ohkawa, Shigenori,Ashida, Yasuko,Maki, Yoshitaka
, p. 2909 - 2920 (2007/10/02)
General synthetic routes to quinone acids (8), quinone amides (9), quinone alcohols (10), and quinone methylketones (11) with polyprenyl side chains, in which allylic alcohols (3) are employed as the key intermediates, are described.The Claisen rearrangements and the Carrol reactions of the allylic alcohols (3) with ethyl orthoacetate and diketen produced the ethyl esters (4) and the methylketones (5), respectively.Quinone products (8), (10), and (11) were recovered by oxidative demethylation of hydroquinone dimethyl ethers (4), (5), and (7) or by acid hydrolysis of hydroquinone bis(methoxymethyl) ethers (4) and (5) followed by ferric chloride oxidation.Amidation of quinone acids (8) led to the formation of quinone amides (9).Inhibitory effects of these quinone derivatives on the generation of the slow reacting substance of anaphylaxis (SRS-A) in the lungs of sensitised guinea pigs are evaluated.
Intermediates for the production of quinones
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, (2008/06/13)
A novel method for producing hydroquinone and quinone derivatives by a regio- and stereo-specific coupling reaction of hydroquinone derivative having a terminal activated (poly)prenyl side chain with a prenyl derivative. This method can provide in good yield various hydroquinone and quinone derivatives having any prenyl length of the side chain.
