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Addition of functionalized organolithium reagents to p-benzoquinones and cyclohexadienones: synthesis of functionalized cyclohexadienones, dienols and dienediols

✍ Scribed by Alfred Fischer; George Narayanan Henderson

Book ID: 104216874
Publisher: Elsevier Science
Year: 1983
Tongue: French
Weight: 249 KB
Volume: 24
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)81347-7

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✦ Synopsis

Low temperature addition of functionalized alkyllithium reagents to p-benzoquinones produces 4-alkyl-4-hydroxycyclohexa-2,5-dienones, and reaction of excess of the reagents with quinones yields 1,4-dialkylcyclohexa-2,5-diene-1,4-diols.

With 4-acetoxy-, 4hydroxy-, and 4-methoxy-4lnethylcyclohexa-2,5-dienones the corresponding dienols are obtained A one-step synthesis of the antibiotics 4-acetamido-and 4-[(ethoxycarbonyl)methyl]-2,6dibromo-4-hydroxycyclohexadienones, and the anti-tumour agent jacaranone is described.

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