- Alternative synthesis of 2-hydroxy-3,5,5-trimethylcyclopent-2-en-1-one
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The 2-hydroxy-3,5,5-trimethylcyclopent-2-en-1-one (1) was synthesized in 42% yield by rearrangement of epoxy ketone 10 on treatment with BF3 ? Et2O under anhydrous conditions. Intermediate 10 was available from the known enone 8, either via direct epoxidation (60% H2O 2 , NaOH, MeOH; yield 50%), or via reduction to the corresponding allylic alcohol 14 (LiAlH4, THF), followed by epoxidation ([VO(acac)2], tBuOOH) and reoxidation under Swern conditions, in 37% total yield.
- Chapuis, Christian,Saint-Leger, Christine
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scheme or table
p. 111 - 117
(2010/04/01)
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- Trisubstituted Stannyllithium as a Double Electron Equivalent. Reaction with α,β-Enones
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β-Stannyl ketones, easily available by the conjugate addition of (trimethylstannyl)lithium to α,β-enones, produced two types of ketones depending upon the substitution pattern by the treatment with titanium(IV) chloride.All the reactions proceeded through an intermediacy of cyclopropanol derivatives.The reaction involving the carbon skeleton rearrangement is promising as a synthetic method.
- Sato, Tadashi,Watanabe, Masami,Watanabe, Toshiyuki,Onoda, Yasuo,Murayama, Eigoro
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p. 1894 - 1899
(2007/10/02)
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