- Oxidative dearomatization and unusual intramolecular Diels-Alder reaction of cyclohexa-2,4-dienone: Synthesis and photoreaction of oxa-tricyclo[5.2.2.01,5]undec-10-ene-8-ones
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Abstract An efficient synthesis of annulated bicyclo[2.2.2]octane having β,γ-enone chromophoric system and triplet sensitized 1,2-acyl shift rearrangement leading to the formation of angular oxa-triquinane is described. Oxidative dearomatization, intramolecular Diels-Alder reaction of 6,6-spiroepoxycyclohexa-2,4-dienone and oxa-di-π-methane reaction are the key features of our approach.
- Das, Beauty,Singh, Vishwakarma
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p. 1982 - 1985
(2015/03/30)
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- Synthesis and Absolute Configuration of Pyriculol
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A total synthesis of optically active pyriculol is described.The Wittig reaction between an aldehyde 19 and a triphenylphosphonium ylide 12 gave an intermediate 20.Successive treatment of 20 with p-toluenesulfonic acid, active manganese dioxide, and potassium carbonate gave (3'R,4'S)-pyriculol (23), which was identical with natural pyriculol (1) in all respects.From this synthesis the absolute stereochemistry of pyriculol (1) was determined to be 2--6-hydroxybenzaldehyde.
- Suzuki, Masanobu,Sugiyama, Takeyoshi,Watanabe, Masashi,Murayama, Tetsuya,Yamashita, Kyohei
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p. 1121 - 1128
(2007/10/02)
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