Oxidation of o-Methoxyphenols with a Hypervalent Iodine Reagent: Improved Synthesis of Asatone and Demethoxyasatone

✍ Scribed by László Kürti; László Szilágyi; Sándor Antus; Mihály Nógrádi

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 207 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199910)1999:10<2579::aid-ejoc2579>3.0.co;2-h

✦ Synopsis

Oxidation of the 2-methoxyphenols 1c-f with phenyl-Using this method the synthesis of asatone (5a) and its demethoxy analogue (5b) was also accomplished starting iodonium(III) diacetate (PIDA) in methanol resulted in the formation of the cyclohexa-2,4-dienones 4c-f, which dime-from the readily available phenol derivatives 1a and 1b, respectively. rized spontaneously to a single product (5c-f) in each case.