- Versatile Route to centro-Substituted Triquinacene Derivatives: Synthesis of 10-Phenyltriquinacene
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(Equation Presented) A versatile route to prepare centro-substituted triquinacene derivatives (1, R = various substituents), as exemplified by the preparation of 10-phenyltriquinacene (1, R = Ph), is reported. The quaternary, centro substituent (C-10) was installed by a trimethylsilyl chloride-promoted conjugate addition reaction of an organocuprate, derived from phenylmagnesium bromide, and the protected bicyclic enone (11). The resultant trimethylsilyl enol ether was then converted regioselectively to the C-2-allylated conjugate addition products (13, R = Ph). The allyl moiety, following oxidative cleavage of the carbon-carbon double bond, was used to elaborate the tricyclic ring system by an intramolecular aldol/ acetal deprotection reaction. The product of this reaction was then converted to the target compound using a standard series of functional group transformation reactions.
- Cadieux, Jay A.,Buller, Donovan J.,Wilson, Peter D.
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- Synthesis of functionalized pentalenes via carbonyl-ene reaction and enzymatic kinetic resolution
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The synthesis of functionalized pentalene derivatives is described. Bicyclo[3.3.0]octane-3,7-dione 5 (Weiss diketone) was converted in six steps into the silyl-protected 3-methylbicyclo[3.3.0]octenol 6, which was submitted to Lewis acid catalyzed carbonyl
- Anderl, Timo,Emo, Marc,Laschat, Sabine,Baro, Angelika,Frey, Wolfgang
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p. 1619 - 1627
(2009/04/06)
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- SYNTHESIS OF cis-BICYCLOOCT-3-ENE-2,7-DIONE, A HIGHLY FUNCTIONALIZED CYCLOPENTANOID INTERMIDIATE
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cis-Bicyclooct-3-ene-2,7-dione (1) has been synthesized either from cis-bicyclooctane-3,7-dione (2) or the -cycloadduct 10 of 5-trimethylsilylcyclopentadiene with dichloroketene.As anticipated, the conjugated double bond of acetal 9 act
- Carceller, Elena,Moyano, Albert,Serratosa, Felix
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p. 2031 - 2034
(2007/10/02)
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