92007-38-0Relevant articles and documents
Versatile Route to centro-Substituted Triquinacene Derivatives: Synthesis of 10-Phenyltriquinacene
Cadieux, Jay A.,Buller, Donovan J.,Wilson, Peter D.
, p. 3983 - 3986 (2003)
(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.
Bifunctinal reagents in organic synthesis. Total syntheses of the sesquiterpenoids (±)-pentalenene and (±)-9-epi-pentalenene
Piers,Karunaratne
, p. 160 - 164 (2007/10/02)
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