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Synlett 1997; 1997(3): 310-312
DOI: 10.1055/s-1997-5787
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Oxidative Intramolecular [4+2]Cycloaddition of o-[(ω-Phenylthioethynyl)acyl]phenols Followed by the Aromatic Pummerer-type Reaction: A Novel Preparation of the peri-Hydroxy Dihydroquinone Structure

Shuji Akai, Kiyosei Iio, Yoshifumi Takeda, Hiroshi Ueno, Yasujuki Kita*
  • *Faculty of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565, Japan, Fax +81 6-879-8229; E-mail kita@phs.osaki-u.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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The combination of the oxidative intramolecular [4+2]cycloaddition of o-acylphenol derivatives 10a,b and 16 having the ω-phenylthioethynyl group in the acyl chain and the Pummerer-type reaction of the cyclization products afforded the peri-hydroxy dihydroquinones 9a,b and 18 in good overall yields.

intramolecular [4+2]cycloaddition - Pummerer-type reaction - peri-hydroxy dihydroquinone - phenylthioacetylene

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